2,4,6-Trimethylpyridine → HCID 20036331, compound

Participants

Reaction Conditions

Reaction Steps

To a 1 L, 3-necked round bottom flask equipped with a reflux condenser, nitrogen inlet, magnetic stirring bar and addition funnel were fed 6-(1-methylpiperidin-4-yl)-1,2,6,7-tetrahydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (19.3 gm), collidine (622 gm) and dichloromethane (500 ml). The mixture was heated to a gentle reflux and alpha-chloroethyl chloroformate (19 gm) was added dropwise over a period of 30 minutes at refluxing temperature. The resultant solution was refluxed for 2 hours and thereafter cooled to about 50° C. The solution was concentrated to a solid-oil mixture and thereafter extracted with ether (about 2 L). The insolubles were filtered off and the ethereal solution was concentrated and dried on a rotary evaporator (high vacuum pump at about 80° C.) until little collidine was left. The crude product (43 gm) was identified as the bis-alpha-chloroethyl carbamate of the desired product.

Provenance & Evidence