Sodium triacetoxyborohydride → HCID 25255734, compound

HRID 1942337Notes

Reaction equation

HRID 1942337 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=[CH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([N:4]([CH:5]1[CH2:13][CH2:12][C:8]2[N:9]=[CH:10][S:11][C:7]=2[CH2:6]1)[CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10352536N-(4-oxo-butyl)-benzamideHCID 18705889Propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amine

Product 1

HCID 25255734HCID 25255734, compoundYield 94%

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 478 mg (2.5 mmol) N-(4-oxo-butyl)-benzamide 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 eluting with dichloromethane/methanol (98:2). The methanol used is saturated with NH3-gas. Evaporation of the solvent yields 1.88 mmol (700 mg) of a colorless viscous oil. The salt of maleic acid is crystallized from acetonitrile/diethylether.

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
  4. customThe crude product obtained
  5. customis purified via column chromatography on silica gel eluting with dichloromethane/methanol (98:2)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a3107462be2849dd9d672771adf9405a
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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