Hydrochloric Acid → 2-(Thiophen-3-yl)ethan-1-amine hydrochloride

Slowly add borane methyl sulfide complex (30.4 mL, 304.4 mmol) to a solution of thiophen-3-yl-acetonitrile (25.0 g, 203.0 mmol) in tetrahydrofuran (450 mL). Heat the reaction at reflux for 16 h and then cool to RT. Slowly quench the reaction with methanol (50 mL) until no foaming is observed. To this mixture slowly add methanol (100 mL) which is saturated with hydrogen chloride. Stir the mixture at RT for 20 min before concentrating in vacuo. Add methanol (100 mL) to the mixture and concentrate in vacuo. Suspend the resulting solid in diethyl ether (200 mL) and filter to afford 31.1 g (94%) of the crude title compound. MS/ES m/z 128.3 [M+H]+.

1. temperatureHeat
2. customthe reaction
3. temperatureat reflux for 16 h
4. customSlowly quench
5. customthe reaction with methanol (50 mL) until no foaming
6. concentrationbefore concentrating in vacuo
7. concentrationAdd methanol (100 mL) to the mixture and concentrate in vacuo
8. filtrationfilter

ORD record

ord-0be59d4283054f8e8266a1ae6194965b

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263772B2