1-((4-Chlorophenyl)methyl)piperidin-4-amine → N-(2-{(2R)-3-[1-(4-Chloro-benzyl)-piperidin-4-ylamino]-2-hydroxy-2-methylpropoxy}-phenyl)-acetamide

HRID 1072501Notes

Reaction equation

HRID 1072501 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[CH3:16][C@:17]1([CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[NH:28][C:29](=[O:31])[CH3:30])[CH2:19][O:18]1>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH:10]([NH:13][CH2:19][C@:17]([OH:18])([CH3:16])[CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH:28][C:29](=[O:31])[CH3:30])[CH2:11][CH2:12]2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 71308331-((4-Chlorophenyl)methyl)piperidin-4-amineHCID 86597619N-(2-{[(2R)-2-Methyloxiranyl]methoxy}phenyl)acetamide

Product 1

HCID 10182107N-(2-{(2R)-3-[1-(4-Chloro-benzyl)-piperidin-4-ylamino]-2-hydroxy-2-methylpropoxy}-phenyl)-acetamideYield 105.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(4-chlorobenzyl)-4-piperidinamine (62 mg, 0.276 mmol) and N-(2-{[(2R)-2-methyloxiranyl]methoxy}phenyl)acetamide (61 mg, 0.276 mmol) in ethanol (1.5 ml) was stirred in a sealed vial at 80° C. for 4 hours. The reaction mixture was diluted with water and purified by reversed phase HPLC to give 130 mg (70%) of the title compound as a ditrifluoroacetate after lyophilisation. The optical purity was determined to 86% ee, by chiral HPLC on a Chiralpak AD-column.

Workup

  1. custompurified by reversed phase HPLC

Sources & evidence

ORD record
ord-f7a4eb3793b6433d83cc46d986c14cdd
Source dataset
uspto-grants-2005_06
Patent number
US06911458B2

Reaction notes

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