Dibah → HCID 86753143, compound
Reaction equation
Cl.[CH3:2][N:3]([CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19]C)[OH:12])[CH3:4].[Cl:21]CCl.[OH-].[Na+].C([Al]CC(C)C)C(C)C>CCOCC>[ClH:21].[CH3:4][N:3]([CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])[OH:12])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Starting from (RS)-2-dimethylaminomethyl-cyclohexanone and 1-bromo-2-methoxy-benzene, (1RS,2RS)-2-dimethylaminomethyl-1-(2-methoxy-phenyl)-cyclohexanol hydrochloride (30) was obtained, under the conditions given in Example 1 (1st step) and using ether as a solvent, in a yield of 47%. The base was released from (30) with dichloromethane/sodium hydroxide solution. After drying the solution, the dichloromethane was distilled off under vacuum. 30.0 g (0.1 mole) of the base were reacted with diisobutylaluminium as in Example 2. 22.7 g (78% theoretical) (1RS,2RS)-2-(2-dimethylaminomethyl-1-hydroxy-cyclo-hexyl-phenol hydrochloride (31) were obtained, with a melting point of 168°-170° C. 28.6 g (0.1 mole) of compound (31) were reacted with 450 ml of concentrated formic acid as in Example 5. The crude base obtained was introduced on to a column packed with silica gel and eluted with 7:1 diisopropyl ether/methanol. 21 g base were obtained, from which 18.6 g (69% theoretical) of hydrochloride (29), which had a melting point of 168° C., was obtained with concentrated hydrochloric acid in acetone.
Workup
- customAfter drying the solution
- distillationthe dichloromethane was distilled off under vacuum
Sources & evidence
- ORD record
- ord-abd06ffb8543450d873a4a629651fef9
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05811582
Reaction notes
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