HCID 67187513, compound → 3-(4-Amino-4-methyl-pentyl)-4-fluoro-1-methyl-1,3-dihydro-benzimidazol-2-one

HRID 33396Notes

Reaction equation

HRID 33396 reaction equation
[F:1][C:2]1[C:10]2[N:9]([CH2:11][CH2:12][CH2:13][C:14]([CH3:19])([N+:16]([O-])=O)[CH3:15])[C:8](=[O:20])[N:7]([CH3:21])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Ni]>[NH2:16][C:14]([CH3:19])([CH3:15])[CH2:13][CH2:12][CH2:11][N:9]1[C:10]2[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=2[N:7]([CH3:21])[C:8]1=[O:20]

Participants

5

Reactant 2

HCID 67187513HCID 67187513, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 597964593-(4-Amino-4-methyl-pentyl)-4-fluoro-1-methyl-1,3-dihydro-benzimidazol-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 2 g (6.7 mmol) 4-fluoro-1-methyl-3-(4-methyl-4-nitro-pentyl)-1,3-dihydro-benzimidazol-2-one in methanol is hydrogenated at 3 bar hydrogen pressure in the presence of Raney nickel. After separation of the catalyst hydrochloric acid in diethyl ether is added. The hydrochloride precipitated is filtered off and dried. Yield: 1.5 g (83%, hydrochloride); melting range=230-232° C.; mass spectroscopy: [M+H]+=303.

Workup

  1. customAfter separation of the catalyst hydrochloric acid in diethyl ether
  2. additionis added
  3. customThe hydrochloride precipitated
  4. filtrationis filtered off
  5. customdried

Sources & evidence

ORD record
ord-4d128cccbb834d8680eeebdf7f6d79eb
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Reaction notes

Loading…