Cyclohexene oxide → (+/-)-N-[trans-1-(2-hydroxy-cyclohexyl)-piperidin-4-yl]-3-methoxy-N-p-tolyl-benzamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[C:6]([N:8]([CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=[O:7].[CH:25]12[O:31][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30]2>>[OH:31][C@@H:26]1[CH2:27][CH2:28][CH2:29][CH2:30][C@H:25]1[N:19]1[CH2:18][CH2:17][CH:16]([N:8]([C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)[C:6](=[O:7])[C:5]2[CH:22]=[CH:23][CH:24]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:21][CH2:20]1Participants
3
Procedure
The title compound, MS (ISP): m/e=499.0 (M+H+), was prepared as for example 141, steps (A) to (F). Step (B) was performed using 3-methoxybenzoyl chloride, and yielded 4-[(3-methoxy-benzoyl)-p-tolyl-amino]-piperidine-1-carboxylic acid tert-butyl ester. This was then deprotected to 3-methoxy-N-piperidin-4-yl-N-p-tolyl-benzamide (step C), and reacted with cyclohexene oxide to give (+/−)-N-[trans-1-(2-hydroxy-cyclohexyl)-piperidin-4-yl]-3-methoxy-N-p-tolyl-benzamide [step (D)]. Oxidation to (+/−)-3-methoxy-N-[1-(2-oxo-cyclohexyl)-piperidin-4-yl]-N-p-tolyl-benzamidein step (E) and reaction with phenyl lithium [step (F)] led to the title compound of the example.
Sources & evidence
- ORD record
- ord-11175f6a690b460fa4615792d816097a
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07176316B2
Reaction notes
Loading…