4-[4-(alpha-Cyclohexyl-alpha-hydroxybenzyl)piperidino]4'-tert-butylbutyrophenone hydrochloride → alpha-(4-Tert-butylphenyl)-4-(alpha-cyclohexyl-alpha-hydroxybenzyl)-1-piperidinebutanol
Reaction equation
Cl.[CH:2]1([C:8]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=3)=[O:26])[CH2:18][CH2:17]2)([OH:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.C(C1C=CC(C(C2CCN(CCCC(C3C=CC=CC=3)=O)CC2)(O)C2C=CC=CC=2)=CC=1)(C)(C)C>>[C:33]([C:30]1[CH:29]=[CH:28][C:27]([CH:25]([OH:26])[CH2:24][CH2:23][CH2:22][N:19]2[CH2:18][CH2:17][CH:16]([C:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)([OH:15])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:21][CH2:20]2)=[CH:32][CH:31]=1)([CH3:36])([CH3:34])[CH3:35]Participants
3
Reactant 2
Product 1
Procedure
When in the procedure of Example 1 an appropriate amount of 4-[4-(α-cyclohexyl-α-hydroxybenzyl)piperidino]4'-tert-butylbutyrophenone hydrochloride is substituted for 4-[4-[α-(p-tert-butylphenyl)-α-hydroxybenzyl]piperidino]butyrophenone hydrochloride and the reaction mixture is refluxed for three hours, α-(4-tert-butylphenyl)-4-(α-cyclohexyl-α-hydroxybenzyl)-1-piperidinebutanol is obtained, M.P. 75°-81°C. This compound was converted to the the hydrochloride salt, M.P. 240°-242.5°C. (dec.) by the usual methods.
Workup
- temperaturethe reaction mixture is refluxed for three hours
Sources & evidence
- ORD record
- ord-7b6343a3f980436e8502ced9e830a2f8
- Source dataset
- uspto-grants-1976_03
- Patent number
- US03941795
Reaction notes
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