Acetic Anhydride → N-[2-(1-Benzyl-piperidin-4-ylamino)-5-fluorophenyl]-propionamide

HRID 2240278Notes

Reaction equation

HRID 2240278 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[NH2:22])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:26][C:27](=O)[CH3:28])(=O)C.[C:30](OCC)(=O)C>>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[NH:22][C:27](=[O:26])[CH2:28][CH3:30])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 211930651-Benzyl-4-(2-amino-4-fluorophenylamino)-piperidine

Product 1

HCID 58599525N-[2-(1-Benzyl-piperidin-4-ylamino)-5-fluorophenyl]-propionamide

Procedure

To a stirred solution of 1-Benzyl-4-(2-amino-4-fluoro-phenylamino)-piperidine (6 g) in ethyl acetate (50 ml) at room temperature was added acetic anhydride (3.3 ml). After 2 h, the reaction was concentrated in vacuo, and the crude oil partitioned between 2:1 DCM and water (150 ml) which was made alkaline with NaOH(aq). The organic layer was separated, washed with water and dried followed by in vacuo concentration to yield 7 g of the title compound as a yellow oil. The compound was used without further purification.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customthe crude oil partitioned between 2:1 DCM and water (150 ml) which
  3. customThe organic layer was separated
  4. washwashed with water
  5. customdried
  6. concentrationfollowed by in vacuo concentration

Sources & evidence

ORD record
ord-7e07e124817d457f8636d24e06f379e1
Source dataset
uspto-grants-2010_05
Patent number
US07723360B2

Reaction notes

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