Sqlite error near where syntax error

(env) [root@chat synapse]# synctl start
Starting ...
This server is configured to use 'matrix.org' as its trusted key server via the
'trusted_key_servers' config option. 'matrix.org' is a good choice for a key
server since it is long-lived, stable and trusted. However, some admins may
wish to use another server for this purpose.

To suppress this warning and continue using 'matrix.org', admins should set
'suppress_key_server_warning' to 'true' in homeserver.yaml.
--------------------------------------------------------------------------------
2019-10-24 13:40:10,455 - twisted - 171 - INFO - None - Redirected stdout/stderr to logs
2019-10-24 13:40:10,455 - root - 236 - WARNING - None - ***** STARTING SERVER *****
2019-10-24 13:40:10,455 - root - 237 - WARNING - None - Server /var/www/synapse/env/lib/python3.6/site-packages/synapse/app/homeserver.py version 1.4.1
2019-10-24 13:40:10,456 - root - 238 - INFO - None - Server hostname: matrix.omnichat.tech
2019-10-24 13:40:10,457 - synapse.app.homeserver - 359 - INFO - None - Preparing database: sqlite3...
2019-10-24 13:40:16,312 - synapse.storage.prepare_database - 249 - INFO - None - Upgrading schema to v55
2019-10-24 13:40:16,313 - synapse.storage.prepare_database - 287 - INFO - None - Applying schema 55/access_token_expiry.sql
2019-10-24 13:40:16,314 - synapse.storage.prepare_database - 287 - INFO - None - Applying schema 55/track_threepid_validations.sql
2019-10-24 13:40:16,316 - synapse.storage.prepare_database - 287 - INFO - None - Applying schema 55/users_alter_deactivated.sql
2019-10-24 13:40:16,316 - synapse.storage.prepare_database - 249 - INFO - None - Upgrading schema to v56
2019-10-24 13:40:16,317 - synapse.storage.prepare_database - 287 - INFO - None - Applying schema 56/add_spans_to_device_lists.sql
2019-10-24 13:40:16,318 - synapse.storage.prepare_database - 287 - INFO - None - Applying schema 56/current_state_events_membership.sql
2019-10-24 13:40:16,318 - synapse.storage.prepare_database - 287 - INFO - None - Applying schema 56/current_state_events_membership_mk2.sql
2019-10-24 13:40:16,319 - synapse.storage.prepare_database - 287 - INFO - None - Applying schema 56/destinations_failure_ts.sql
2019-10-24 13:40:16,320 - synapse.storage.prepare_database - 287 - INFO - None - Applying schema 56/devices_last_seen.sql
2019-10-24 13:40:16,322 - synapse.storage.prepare_database - 287 - INFO - None - Applying schema 56/fix_room_keys_index.sql
2019-10-24 13:40:16,323 - synapse.storage.prepare_database - 287 - INFO - None - Applying schema 56/redaction_censor.sql
2019-10-24 13:40:16,324 - twisted - 171 - ERROR -  - Traceback (most recent call last):
2019-10-24 13:40:16,325 - twisted - 171 - ERROR -  -   File "/usr/lib64/python3.6/runpy.py", line 193, in _run_module_as_main
2019-10-24 13:40:16,326 - twisted - 171 - ERROR -  -     "__main__", mod_spec)
2019-10-24 13:40:16,326 - twisted - 171 - ERROR -  -   File "/usr/lib64/python3.6/runpy.py", line 85, in _run_code
2019-10-24 13:40:16,326 - twisted - 171 - ERROR -  -     exec(code, run_globals)
2019-10-24 13:40:16,326 - twisted - 171 - ERROR -  -   File "/var/www/synapse/env/lib/python3.6/site-packages/synapse/app/homeserver.py", line 659, in <module>
2019-10-24 13:40:16,327 - twisted - 171 - ERROR -  -     main()
2019-10-24 13:40:16,327 - twisted - 171 - ERROR -  -   File "/var/www/synapse/env/lib/python3.6/site-packages/synapse/app/homeserver.py", line 654, in main
2019-10-24 13:40:16,328 - twisted - 171 - ERROR -  -     hs = setup(sys.argv[1:])
2019-10-24 13:40:16,328 - twisted - 171 - ERROR -  -   File "/var/www/synapse/env/lib/python3.6/site-packages/synapse/app/homeserver.py", line 363, in setup
2019-10-24 13:40:16,329 - twisted - 171 - ERROR -  -     prepare_database(db_conn, database_engine, config=config)
2019-10-24 13:40:16,329 - twisted - 171 - ERROR -  -   File "/var/www/synapse/env/lib/python3.6/site-packages/synapse/storage/prepare_database.py", line 74, in prepare_database
2019-10-24 13:40:16,329 - twisted - 171 - ERROR -  -     _setup_new_database(cur, database_engine)
2019-10-24 13:40:16,330 - twisted - 171 - ERROR -  -   File "/var/www/synapse/env/lib/python3.6/site-packages/synapse/storage/prepare_database.py", line 171, in _setup_new_database
2019-10-24 13:40:16,330 - twisted - 171 - ERROR -  -     is_empty=True,
2019-10-24 13:40:16,330 - twisted - 171 - ERROR -  -   File "/var/www/synapse/env/lib/python3.6/site-packages/synapse/storage/prepare_database.py", line 288, in _upgrade_existing_database
2019-10-24 13:40:16,331 - twisted - 171 - ERROR -  -     executescript(cur, absolute_path)
2019-10-24 13:40:16,331 - twisted - 171 - ERROR -  -   File "/var/www/synapse/env/lib/python3.6/site-packages/synapse/storage/prepare_database.py", line 427, in executescript
2019-10-24 13:40:16,332 - twisted - 171 - ERROR -  -     txn.execute(statement)
2019-10-24 13:40:16,332 - twisted - 171 - ERROR -  - sqlite3.OperationalError: near "WHERE": syntax error

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When attempting to use the ManyToMany relationship with the following code I get a rather nondescript error on conn.Update(element); in WriteOperations.cs:UpdateWithChildren(SQLiteConnection, object).

The error is: SQLite.Net.SQLiteException: near «where»: syntax error

My code is:

    [Table("Contact")]
    public class Contact
    {
        [PrimaryKey, AutoIncrement]
        public int Id { get; set; }

        [MaxLength(50)]
        public string FirstName { get; set; }

        [MaxLength(50)]
        public string Surname { get; set; }

        [ManyToMany(typeof(Participant))]
        public List<Journey> Journeys { get; set; }

    }

    public class Participant
    {
        [ForeignKey(typeof(Contact))]
        public int ContactId { get; set; }

        [ForeignKey(typeof(Journey))]
        public int JourneyId { get; set; }
    }

    [Table("Journey")]
    public class Journey
    {
        [PrimaryKey, AutoIncrement]
        public int Id { get; set; }

        [ManyToMany(typeof(Participant))]
        public List<Contact> Contacts { get; set; }

    }




string dbPath = Path.Combine(Environment.GetFolderPath(Environment.SpecialFolder.Personal), "xandroid.db3");

var db = new SQLiteConnection(platform, dbPath);

db.DropTable<Contact>();
db.DropTable<Participant>();
db.DropTable<Journey>();
db.CreateTable<Contact>();
db.CreateTable<Participant>();
db.CreateTable<Journey>();

Contact beans = new Contact { FirstName = "Beans", Surname = "Connor" };
Contact winston = new Contact { FirstName = "Winston", Surname = "Connor" };
var contacts = new List<Contact> { beans, winston };
db.InsertAllWithChildren(contacts);

Journey returnHome = new Journey { Contacts = contacts };
db.InsertAllWithChildren(new List<Journey> { returnHome }, recursive: true);

The error occurs on the final call to db.InsertAllWithChildren for the Journey objects.