Acetic Anhydride → 1-Benzyl-3-acetamidopyrrolidine

HRID 1382754Notes

Reaction equation

HRID 1382754 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3]1.[C:14](OC(=O)C)(=[O:16])[CH3:15].[OH-].[Na+]>C(Cl)Cl>[C:14]([NH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3]1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 27566131-Benzyl-3-aminopyrrolidine

Product 1

HCID 41983391-Benzyl-3-acetamidopyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-1-benzylpyrrolidine [8.3 g, prepared by a method of G. C. Helsley et al., J. Med. Chem., 11, 1034 (1968)] was dissolved in methylene chloride (40 ml) and thereto acetic anhydride (5.3 g) was added dropwise with stirring under cooling with ice-water and the mixture was stirred for 1.5 hours. After addition of 2N sodium hydroxide (40 ml), the mixture was extracted with methylene chloride. The extract was washed with water and dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure to give 3-acetylamino-1benzylpyrrolidine (9.0 g) as oil.

Workup

  1. stirringthe mixture was stirred for 1.5 hours
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-0737739d98af477188f59651a1809b48
Source dataset
uspto-grants-1989_02
Patent number
US04808584

Reaction notes

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