Ethanol → 2-(Dimethylaminophenylmethyl)cyclohexanol
Reaction equation
[CH3:1][N:2]([CH:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11])[CH3:3].[H-].C([Al+]CC(C)C)C(C)C.C(O)C.O>C1(C)C=CC=CC=1>[CH3:3][N:2]([CH:4]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[OH:11])[CH3:1]Participants
Procedure
3.0 g (13.0 mmole) of the 2-(dimethylaminophenyl-methyl)cyclohexanone prepared according to Example 1 (2nd stage), dissolved in 26 ml toluene, were added dropwise to 26 ml (39 mmole) diisobutylaluminium hydride (1.5 M in toluene) at RT under nitrogen. The mixture was heated under reflux for 15 hours, while stirring. For working up, 13 ml ethanol and 13 ml water were slowly added dropwise and the suspension was stored at 0° C. for several hours, filtered through a glass frit and washed several times with a little toluene. The filtrate was concentrated on a rotary evaporator (500 to 10 mbar) and residues of solvent were removed under a high vacuum (approx. 0.1 mbar). 2.62 g (86.6% of theoretical) 2-(dimethylaminophenylmethyl)-cyclohexanol were obtained.
Workup
- temperatureThe mixture was heated
- temperatureunder reflux for 15 hours
- waitthe suspension was stored at 0° C. for several hours
- filtrationfiltered through a glass frit
- washwashed several times with a little toluene
- concentrationThe filtrate was concentrated on a rotary evaporator (500 to 10 mbar) and residues of solvent
- customwere removed under a high vacuum (approx. 0.1 mbar)
Sources & evidence
- ORD record
- ord-e5ae0245ecf44353a171709c1a3a409b
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06288278B1
Reaction notes
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