Cyclohexanone → HCID 16667155, compound
Reaction equation
C[N:2](CC(C1(O)CCCCC1)C1C=CC(O)=CC=1)C.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]#N)=[CH:24][CH:23]=1.[C:31]1(=[O:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.[OH-].[Na+]>>[C:32]([C:31]1([OH:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH:29]1[CH2:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[CH:27][CH:26]=1)#[N:2]Participants
Procedure
WO 2007/094008 application discloses a process for the preparation of O-desmethylvenlafaxine, wherein p-methoxyphenyl acetonitrile is reacted with cyclohexanone in presence of sodium hydroxide and phase transfer catalyst selected from polyethyleneglycol-400 or ALIQUATE 336™ (N-methyl-N,N-dioctyloctan-1-ammonium chloride) to give 1-cyano[(4-methoxyphenyl)methyl] cyclohexanol, which is further subjected to reduction reaction in the presence of reducing agent such as borane-dimethylsulphide complex, aluminum chloride-sodium borohydride to give 1-[2-amino-1-(4methoxyphenyl)ethyl]cyclohexanol. Subsequently, 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol is subjected to reductive aviation reaction in presence of formic acid and formaldehyde to give venlafaxine.
Sources & evidence
- ORD record
- ord-62317e81aac44ce587099933494b19d6
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304578B2
Reaction notes
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