Acetic Anhydride → (1r-trans)-n-[2-(3,4-Difluorophenyl)cyclopropyl]acetamide

HRID 50642Notes

Reaction equation

HRID 50642 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[F:8][C:9]1[CH:10]=[C:11]([C@@H:16]2[CH2:18][C@H:17]2[NH2:19])[CH:12]=[CH:13][C:14]=1[F:15].OC(C(O)C([O-])=O)C([O-])=O.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>O1CCCC1>[F:8][C:9]1[CH:10]=[C:11]([C@@H:16]2[CH2:18][C@H:17]2[NH:19][C:5](=[O:7])[CH3:6])[CH:12]=[CH:13][C:14]=1[F:15]

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 38061142,3-DihydroxybutanedioateHCID 9834068(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine

Product 1

HCID 69887260(1r-trans)-n-[2-(3,4-Difluorophenyl)cyclopropyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic anhydride (0.31 ml) was added to a suspension of (1R-trans)-2-(3,4-difluorophenyl)cyclopropanamine, (R-(R*,R*)]-2,3-dihydroxybutanedioate (1:1) (prepared as described in International Patent Application WO 9905143) (700 mg) and potassium carbonate (1.0 g) in tetrahydrofuran (20 ml) and stirred for 20 h. Saturated ammonium chloride solution was added and the mixture was extracted with ether and the organic layers were dried (MgSO4) and evaporated to afford the sub-title compound (470 mg).

Workup

  1. extractionthe mixture was extracted with ether
  2. dry with materialthe organic layers were dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-e5640ab26898412dae32d8e60d984a6f
Source dataset
uspto-grants-2004_03
Patent number
US06713483B1

Reaction notes

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