1-((2-Hydroxyethyl)(methyl)amino)-3-(1-nitrocyclohexyl)propan-2-ol → 1-(1-Aminocyclohexyl)-3-((2 hydroxyethyl)(methyl)amino)propan-2-ol

A 300 mL Parr autoclave is charged with methanol (100 mL), Raney Nickel catalyst (R-3111, 6.8 g wet weight) and compound (13) (20.8 g crude) dissolved in 100 mL MeOH. The reactor is sealed, purged with nitrogen followed by purging with hydrogen and then brought up to 60° C. under 400 psi hydrogen pressure. When the temperature reaches 60° C., the reactor pressure is increased to approximately 450 psi. The reaction is stopped when no more hydrogen is consumed in the reaction. The entire reaction takes 1-1.5 h to reach completion. After cooling to room temperature, the reactor is vented, opened and the catalyst isolated via vacuum filtration. The brown filtrate is stripped on a rotary evaporator (50-55° C./28-29″ vacuum) to remove water/methanol. The above process provides 6.4 g of the crude mixture. The desired material, compound (14) is eluted in GC-MS EI at retention time of 22.7 minutes, however the molecular ion peak cannot not be seen due to fragmentation in the GC. The presence of 1-(1-aminocyclohexyl)-3-((2 hydroxyethyl) (methyl)amino)propan-2-ol (14) is identified by LC/MS with [M+H]=231.20.

1. customThe reactor is sealed
2. custompurged with nitrogen
3. customby purging with hydrogen
4. custombrought up to 60° C. under 400 psi hydrogen pressure
5. customreaches 60° C.
6. temperaturethe reactor pressure is increased to approximately 450 psi
7. customis consumed in the reaction
8. customThe entire reaction
9. customthe catalyst isolated via vacuum filtration
10. customThe brown filtrate is stripped on a rotary evaporator (50-55° C./28-29″ vacuum)
11. customto remove water/methanol

ORD record

ord-fc799bdfed4941ea84b86e2f6e6be742

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08480800B2