Dimethylamine, hydrochloride → HCID 22609607, compound

Participants

Reaction Steps

Addition of 102 mg (1.8 mmol) of potassium hydroxide to a solution of 479 mg (5.9 mmol) of dimethylamine hydrochloride in methanol (4 ml) gave a clear solution. To this solution were added 979 mg (2.3 mmol) of 1,4-bis(p-toluenesulfonyl)-6-oxohexahydro-1,4-diazepine synthesized by the above process in methanol (30 ml) and 116 mg (1.8 mmol) of sodium cyanoborohydride. After the resultant mixture was stirred for 15 hours at room temperature, 104 mg (1.7 mmol) of additional sodium cyanoborohydride was added, and the mixture was stirred for an additional 25 hours. A 1N aqueous solution (5 ml) of sodium hydroxide was added to the reaction mixture, and the mixture was concentrated under reduced pressure, followed by extraction with chloroform. An organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel to obtain 519 mg (yield: 50%) of 1,4-bis(p-toluenesulfonyl)-6-(N,N-dimethylamino)-hexahydro-1,4-diazepine as a colorless oil.

Provenance & Evidence