Hydrochloric Acid → HCID 21519232, compound
Reaction equation
[OH:1][C:2]1([CH:16]([CH3:20])[C:17](O)=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1.C(OC(=O)C(C1(O)CCCCC1C1C=CC(OC)=CC=1)C)C.OC1(C(C)CO)CCCCC1C1C=CC(OC)=CC=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[CH3:73][NH:74][CH3:75].[ClH:76]>>[ClH:76].[CH3:73][N:74]([CH3:75])[CH2:17][CH:16]([C:2]1([OH:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[CH3:20]Participants
Procedure
The procedure of Example II is followed except that 2-phenylcyclohexanone is replaced by 2-(p-Methoxyphenyl)cyclohexanone and piperidine is replaced by dimethylene. By this method is obtained 196 g crude Ethyl-2-(1-hydroxy-2-[p-methoxyphenyl]cyclohexyl) propionate from 128.7 g 2-(p-Methoxyphenyl)cyclohexanone (which is prepared by known methods) and 121.8 g Ethyl-2-bromopropionate; 50 g crude 2-(1-Hydroxy-2-[p-methoxyphenyl]cyclohexyl) propionic acid from 196 g Ethyl-2-(1-hydroxy-2-[p-methoxyphenyl]cyclohexyl)propionate; 54.6 g crude 2-(1-Hydroxy-2-[p-methoxyphenyl]cyclohexyl)propanol from 50 g 2-(1-Hydroxy-2-[p-methoxyphenyl]cyclohexyl)propionic acid. The crude 2-(1-Hydroxy-2-[p-methoxyphenyl]cyclohexyl)propanol is converted to the tosylate and treated with 125 ml dimethylamine (according to the procedure of Example II) to give 44 g crude base which is converted to the hydrochloride and recrystallized from isopropanol to give 33.5 g product, m. 245-6.
Workup
- customto give 44 g crude base which
- customrecrystallized from isopropanol
Sources & evidence
- ORD record
- ord-16c0592a33c048a4b8c8dcf6dd461f71
- Source dataset
- uspto-grants-1976_08
- Patent number
- US03974157
Reaction notes
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