Potassium Hydroxide → 4-[4-(4-Chlorophenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenylbutanamide

HRID 1669729Notes

Reaction equation

HRID 1669729 reaction equation
[11CH3][NH:2][C:3]([C:5]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][C:11]([OH:21])([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:4].[OH-].[K+]>CC(O)(C)C>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]2([OH:21])[CH2:10][CH2:9][N:8]([CH2:7][CH2:6][C:5]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:3]([NH2:2])=[O:4])[CH2:13][CH2:12]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 251301371067642-12-9

Product 1

HCID 251297954-[4-(4-Chlorophenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenylbutanamideYield 37%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Slow hydrolysis of the alkylation product (compound 1) with KOH in t-BuOH at 100° C. for 2-3 days gave the required precursor (4-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-2,2-diphenylbutanamide; compound 2 in the scheme above) in about 37% yield. Intermediate nitrile and amide precursor were characterized by spectroscopic techniques including 1H and 13C NMR, and LC-MS.

Sources & evidence

ORD record
ord-037f44da8c724701bd0fa09c81c471b5
Source dataset
uspto-grants-2011_08
Patent number
US07989630B2

Reaction notes

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