Sodium triacetoxyborohydride → 4-phenyl-N-(4-(propyl-(4,5,6,7-tetrahydrobenzo [d]thiazol-6-yl)amino)butyl)piperidine-1-carboxamide

HRID 1942390Notes

Reaction equation

HRID 1942390 reaction equation
O=[CH:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)=[O:8].[CH2:21]([NH:24][CH:25]1[CH2:33][CH2:32][C:28]2[N:29]=[CH:30][S:31][C:27]=2[CH2:26]1)[CH2:22][CH3:23].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:15]1([CH:12]2[CH2:13][CH2:14][N:9]([C:7]([NH:6][CH2:5][CH2:4][CH2:3][CH2:2][N:24]([CH2:21][CH2:22][CH3:23])[CH:25]3[CH2:33][CH2:32][C:28]4[N:29]=[CH:30][S:31][C:27]=4[CH2:26]3)=[O:8])[CH2:10][CH2:11]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 18705889Propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amineHCID 86651312N-(4-oxobutyl)-4-phenylpiperidine-1-carboxamide

Product 1

HCID 669374664-phenyl-N-(4-(propyl-(4,5,6,7-tetrahydrobenzo [d]thiazol-6-yl)amino)butyl)piperidine-1-carboxamideYield 34%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 713 mg (2.6 mmol) N-(4-oxobutyl)-4-phenylpiperidine-1-carboxamide and 395 mg (2 mmol) propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amine in 1,2-dichloroethane (20 mL) is stirred for about 30 minutes. Then 0.75 g (3 mmol) of sodium triacetoxyborohydride is added and the mixture is stirred overnight. After hydrolysation with 30 mL of 1N aqueous NaOH solution the organic phase is separated, dried over sodium sulfate and concentrated in vacuum. The crude product obtained is purified via column chromatography on silica gel.

Workup

  1. customAfter hydrolysation with 30 mL of 1N aqueous NaOH solution the organic phase is separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-46f91837a47a44a9a8eb4539a7869135
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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