Sodium borohydride → 4-Aminomethyl-N-(4-chloro-phenyl)-3,N-dimethyl-benzamide

HRID 220974Notes

Reaction equation

HRID 220974 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:20])[C:9](=[O:19])[C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[C:12]([CH3:18])[CH:11]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[NH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]([N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH3:20])=[O:19])=[CH:11][C:12]=1[CH3:18]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 57555280N-(4-chloro-phenyl)-4-cyano-3,N-dimethyl-benzamide

Product 1

HCID 575552204-Aminomethyl-N-(4-chloro-phenyl)-3,N-dimethyl-benzamideYield 70%

Reagents, catalysts & solvents 2

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(4-chloro-phenyl)-4-cyano-3,N-dimethyl-benzamide from Example E115.1 (5.1 g, 17.9 mmol) in methanol (250 ml) was treated with cobalt(II) chloride hexahydrate (8.4 g, 35.8 mmol). The mixture was stirred for 15 min at room temperature then cooled down to 0° C. and sodium borohydride (6.7 g, 179 mmol) was added portionwise. The mixture was stirred for 1 h at room temperature, filtered through Celite® filter agent, washed with methanol and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:10% methanol:89% dichloromethane) to yield the title compound (3.6 g, 70%).

Workup

  1. temperaturethen cooled down to 0° C.
  2. stirringThe mixture was stirred for 1 h at room temperature
  3. filtrationfiltered through Celite®
  4. filtrationfilter agent
  5. washwashed with methanol
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:10% methanol:89% dichloromethane)

Sources & evidence

ORD record
ord-cd59ebc677124cdba443d87ef0dc60ce
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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