Benzoyl chloride → HCID 86594090, compound

HRID 348547Notes

Reaction equation

C(Cl)(=O)C1C=CC=CC=1.C(OC([N:17]1[CH2:22][CH2:21][CH:20]([N:23]([C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)[CH2:19][CH2:18]1)=O)(C)(C)C.ClC1C=CC(N(C2CCNCC2)C(=O)[C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([O:55]C)[CH:50]=2)=CC=1.C12OC1CCCC2>>[OH:55][C@@H:51]1[CH2:52][CH2:53][CH2:54][CH2:49][C@H:50]1[N:17]1[CH2:22][CH2:21][CH:20]([N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)[C:32](=[O:39])[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:19][CH2:18]1

Participants

Reactant 4

HCID 7412Benzoyl chloride

HCID 9246Cyclohexene oxide

HCID 17980050HCID 17980050, compound

HCID 69418536HCID 69418536, compound

Product 1

HCID 86594090HCID 86594090, compound

Procedure

The title compound, MS (ISP): m/e=485.4 (M+H+), was prepared as for example 98, steps (A) to (F). Step (A) was performed using 3-methoxy-aniline, and yielded 4-(3-methoxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester which was acylated with benzoyl chloride to 4-[benzoyl-(3-methoxy-phenyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (B). This was then deprotected to N-(3-methoxy-phenyl)-N-piperidin-4-yl-benzamide (C), and reacted with cyclohexene oxide to gave (+/−)-N-[trans-1-(2-hydroxy-cyclohexyl)-piperidin-4-yl]-N-(3-methoxy-phenyl)-benzamide [step (D)]. Oxidation to (+/−)-N-(3-methoxy-phenyl)-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-af48ca0ce23645c79b75169c7cb9b072
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176316B2

Reaction notes

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