Cyclohexene oxide → HCID 86594088, compound

HRID 348546Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[C:15](=[O:24])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.ClC1C=CC(N(C2CCNCC2)C(=O)[C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([O:47]C)[CH:42]=2)=CC=1.C12OC1CCCC2>>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([N:14]([CH:11]2[CH2:10][CH2:9][N:8]([C@@H:42]3[CH2:41][CH2:46][CH2:45][CH2:44][C@H:43]3[OH:47])[CH2:13][CH2:12]2)[C:15](=[O:24])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=[CH:26][CH:27]=1

Participants

Reactant 3

HCID 9246Cyclohexene oxide

HCID 17980050HCID 17980050, compound

HCID 69421044HCID 69421044, compound

Product 1

HCID 86594088HCID 86594088, compound

Procedure

The title compound, MS (ISP): m/e=519.4 (M+H+), white foam, was prepared as for example 98, steps (A) to (F). Step (A) was performed using 4-chloro-aniline, and yielded 4-(4-chloro-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester which was acylated to 4-[(4-chloro-phenyl)-(3-methoxy-benzoyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester in step (B). This was then deprotected to N-(4-chloro-phenyl)-3-methoxy-N-piperidin-4-yl-benzamide (C), and reacted with cyclohexene oxide to give (+/−)—N-(4-chloro-phenyl)-N-[trans-1-(2-hydroxy-cyclohexyl)-piperidin-4-yl]-3-methoxy-benzamide [step (D)]. Oxidation to (+/−)-N-(4-chloro-phenyl)-3-methoxy-N-[1-(2-oxo-cyclohexyl)-piperidin-4-yl]-benzamide in step (E) and reaction with phenyl lithium [step (F)] led to the title compound of the example.

Sources & evidence

ORD record: ord-4c19511bfa974e77bdf66e4e68d7146c
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176316B2

Reaction notes

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