Dimethylformamide → HCID 59322960, compound

HRID 331217Notes

Reaction equation

HRID 331217 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C@H:7]2[N:12]1[CH2:17][CH2:16][CH:15]([N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[NH:20][C:19]2=[O:27])[CH2:14][CH2:13]1.[H-].[Na+].Br[CH2:31][C:32]([O:34]CC)=O.[CH3:37][N:38](C=O)C>>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C@H:7]2[N:12]1[CH2:17][CH2:16][CH:15]([N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]([CH2:31][C:32]([NH:38][CH3:37])=[O:34])[C:19]2=[O:27])[CH2:14][CH2:13]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 59322917HCID 59322917, compound

Product 1

HCID 59322960HCID 59322960, compound

Procedure

(R)-1-[1-(5-Methyl-1,2,3,4-tetrahydronaphthalen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol 2-one (995 mg) was dissolved in DMF (10 ml). Sodium hydride (132 mg, 60%) was added, and the suspension was stirred at room temperature for 40 min. Ethyl bromoacetate (458 μl) was added, and the mixture was stirred for 4 hr. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated aqueous ammonium chloride solution, dried over sodium sulfate, and concentrated. To the residue was added 40% methylamine-methanol solution (30 ml), the mixture was stirred at room temperature for 2.5 hr, and the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol), and crystallized with ethyl acetate to give the title compound (1.0 g) as pale-yellow crystals.

Workup

  1. stirringthe mixture was stirred for 4 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated aqueous ammonium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. additionTo the residue was added 40% methylamine-methanol solution (30 ml)
  7. stirringthe mixture was stirred at room temperature for 2.5 hr
  8. concentrationthe reaction mixture was concentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)
  10. customcrystallized with ethyl acetate

Sources & evidence

ORD record
ord-2a5da6a7a177481e97c91c55a7a7e0c8
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

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