Sodium triacetoxyborohydride → 1-(4-Phenylpiperazin-1-yl)-5-(propyl-(4,5,6,7-tetrahydrobenzothiazol-6-yl)amino)pentan-1-one

HRID 1942407Notes

Reaction equation

HRID 1942407 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:13][CH2:12][C:8]2[N:9]=[CH:10][S:11][C:7]=2[CH2:6]1)[CH2:2][CH3:3].[O:14]=[C:15]([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)[CH2:16][CH2:17][CH2:18][CH:19]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:27]1([N:24]2[CH2:25][CH2:26][N:21]([C:15](=[O:14])[CH2:16][CH2:17][CH2:18][CH2:19][N:4]([CH2:1][CH2:2][CH3:3])[CH:5]3[CH2:13][CH2:12][C:8]4[N:9]=[CH:10][S:11][C:7]=4[CH2:6]3)[CH2:22][CH2:23]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 18705889Propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amineHCID 866513155-Oxo-5-(4-phenylpiperazin-1-yl)pentanal

Product 1

HCID 426029431-(4-Phenylpiperazin-1-yl)-5-(propyl-(4,5,6,7-tetrahydrobenzothiazol-6-yl)amino)pentan-1-oneYield 67%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 395 mg (2 mmol) propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amine and 781 mg (3 mmol) 5-oxo-5-(4-phenylpiperazin-1-yl)pentanal 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-f2cb6fbce12347f0af63bbe14c311b0d
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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