Ammonia → 6-Dimethylaminohex-4-ynylamine

A flask fitted with a dry ice condenser was charged with liquid ammonia (250 ml). To this was added sodium (0.24 mol) in portions together with a few grains of ferric nitrate; subsequently dimethylaminoprop-2-yne (0.24 mol) was added. The reaction mixture was stirred for one hour, 3-bromopropylamine hydrochloride (0.24 mol) was added in portions and the mixture stirred for a further two hours. Anhydrous diethyl ether (150 ml) was added and excess ammonia was allowed to evaporate overnight. The reaction mixture was dissolved in methanol and evaporated under reduced pressure to afford a residue, which was partitioned between chloroform and water. The aqueous layer was washed with chloroform (5×150 ml). The chloroform extracts were combined, dried over MgSO4, filtered and evaporated under reduced pressure to give 6-dimethylaminohex-4-ynylamine as an oil (5.4 g).

1. customA flask fitted with a dry ice condenser
2. stirringthe mixture stirred for a further two hours
3. customto evaporate overnight
4. dissolutionThe reaction mixture was dissolved in methanol
5. customevaporated under reduced pressure
6. customto afford a residue, which
7. customwas partitioned between chloroform and water
8. washThe aqueous layer was washed with chloroform (5×150 ml)
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. customevaporated under reduced pressure

ORD record

ord-b1ccccb8f75b4e5986fea51b14e45797

Source dataset

uspto-grants-1988_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04732980