Methylamine → rac-(1R,2R)-2-(methylamino)cyclohexan-1-ol

Cyclohexene oxide (202 mL, 2 mol) was added dropwise to aqueous methyl amine (466 mL or 40% solution, 6 mol) over 70 minutes. After a further 90 minutes, the temperature of the reaction mixture was 48° C. and was reduced to 30° C. by cooling in a water bath. After a further 2 hours, the mixture had returned to room temperature. It was stirred overnight, and then refluxed for 3 h. The mixture was saturated with sodium hydroxide (cooled during addition), extracted several times with diethyl ether (total 500 mL), the diethyl ether layer dried over sodium sulphate overnight, and the diethyl ether removed on a rotary evaporator. The remaining diethyl ether and cyclohexene oxide were removed by partial vacuum distillation. Distillation under full vacuum yielded a colorless fraction boiling at 95° C., (±)-trans-2-(methylamino)cyclohexanol: 217 g (84%).

1. customwas 48° C.
2. customwas reduced to 30° C.
3. temperatureby cooling in a water bath
4. waitAfter a further 2 hours
5. customhad returned to room temperature
6. temperaturerefluxed for 3 h
7. extractionextracted several times with diethyl ether (total 500 mL)
8. dry with materialthe diethyl ether layer dried over sodium sulphate overnight
9. customthe diethyl ether removed on a rotary evaporator
10. customThe remaining diethyl ether and cyclohexene oxide were removed by partial vacuum distillation
11. distillationDistillation under full vacuum

ORD record

ord-25ac1325910a446687606c7b01c71d00

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05506257