Benzylamine → cis(+/-)-N-benzyl-3-(2,2-difluoroethoxy)-1-(trifluoroacetyl)piperidin-4-amine

HRID 43690Notes

Reaction equation

HRID 43690 reaction equation
[F:1][CH:2]([F:18])[CH2:3][O:4][CH:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:6]1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:19]([NH:26][C@H:10]1[CH2:9][CH2:8][N:7]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:6][C@H:5]1[O:4][CH2:3][CH:2]([F:18])[F:1])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866486323-(2,2-Difluoroethoxy)-1-(trifluoroacetyl)piperidin-4-one

Product 1

HCID 86648633cis(+/-)-N-benzyl-3-(2,2-difluoroethoxy)-1-(trifluoroacetyl)piperidin-4-amineYield 79.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The same operation as in Example (90c) was performed using 3-(2,2-difluoroethoxy)-1-(trifluoroacetyl)piperidin-4-one obtained in Example (121c) (1.1 g, 4 mmol), benzylamine (0.54 g, 5 mmol), sodium (triacetoxy)borohydride (0.85 g, 6 mmol) and 1,2-dichloroethane (15 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, 1/1, 1/3, 0/1) to obtain 1.16 g of the title compound as a yellow oily substance (79%).

Workup

  1. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, 1/1, 1/3, 0/1)

Sources & evidence

ORD record
ord-a20c46f57dba4a599c2643887e879481
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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