HCID 178465384, compound → HCID 178463402, compound

HRID 1620128Notes

Reaction equation

HRID 1620128 reaction equation
C(OC(=O)[NH:10][CH:11]([C:13]1[NH:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1)[CH3:12])C1C=CC=CC=1>CO.[Pd]>[C:18]1([C:16]2[N:17]=[C:13]([CH:11]([NH2:10])[CH3:12])[NH:14][CH:15]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 178465384HCID 178465384, compound

Product 1

HCID 178463402HCID 178463402, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [1-(4-phenyl-1H-imidazol-2-yl)-ethyl]-carbamic acid benzyl ester (1.5 g, 4.67 mmol) in methanol (25 mL) was added 10% palladium on carbon (0.16 g). The mixture was shaken in a hydrogenation apparatus at it under a hydrogen atmosphere (10 psi) for 8 h. Filtration followed by evaporation to dryness under reduced pressure gave the crude product 1-(4-Phenyl-1H-imidazol-2-yl)-ethylamine (0.88 g, 100%). 1H NMR (300 MHz, CDCl3): δ 1.53 (3H, d), 4.33 (1H, q), 7.23 (3H, m), 7.37 (2H, m), 7.67 (2H, m). MS (ES+): 188.1 (38%).

Workup

  1. filtrationFiltration
  2. customfollowed by evaporation to dryness under reduced pressure

Sources & evidence

ORD record
ord-aa71d31fd48a468d9e3cbaf7098fd402
Source dataset
uspto-grants-2014_07
Patent number
US08772325B2

Reaction notes

Loading…