[(S)-1-(7-Methyl-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid benzyl ester → (S)-1-(7-Methyl-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamine

HRID 242771Notes

Reaction equation

HRID 242771 reaction equation
C(OC(=O)[NH:10][C@H:11]([C:13]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]2[C:24]([CH3:28])=[CH:25][CH:26]=[CH:27][C:15]=2[N:14]=1)[CH3:12])C1C=CC=CC=1>[Pd]>[CH3:28][C:24]1[C:16]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:13]([C@@H:11]([NH2:10])[CH3:12])=[N:14][C:15]=2[CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 1

HCID 68157517[(S)-1-(7-Methyl-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid benzyl ester

Product 1

HCID 68157399(S)-1-(7-Methyl-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamineYield 144.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of [(S)-1-(7-methyl-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid benzyl ester (1.5 g, 3.89 mmol) and 10% Pd/C (150 mg) in IMS (25 mL) was degassed with a stream of nitrogen and, after addition of HCl (1M, 2.5 mL), was stirred at RT (room temperature) under a hydrogen atmosphere for 5.5 h. The suspension was then filtered through a pad of Celite® and the filtrate was concentrated in vacuo. The resulting residue was partitioned between DCM (dichloromethane) and water, the organic layer was then washed with a saturated solution of NaHCO3, dried (Na2SO4) and concentrated in vacuo affording (S)-1-(7-Methyl-1-phenyl-1H-benzoimidazol-2-yl)ethylamine as a brown solid (1.41 g, 96%). LCMS: RT 2.07 min [M−NH2]1 235.1

Workup

  1. customwas degassed with a stream of nitrogen
  2. additionafter addition of HCl (1M, 2.5 mL)
  3. filtrationThe suspension was then filtered through a pad of Celite®
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe resulting residue was partitioned between DCM (dichloromethane) and water
  6. washthe organic layer was then washed with a saturated solution of NaHCO3
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56eba092f02942d19c156367c74371dd
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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