Acetyl chloride → 3-Acetylaminomethyl-1-benzyl-4-chloropyrrolidine

HRID 2232088Notes

Reaction equation

HRID 2232088 reaction equation
[NH2:1][CH2:2][CH:3]1[CH:7]([Cl:8])[CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4]1.[C:16](Cl)(=[O:18])[CH3:17]>C(O)C>[C:16]([NH:1][CH2:2][CH:3]1[CH:7]([Cl:8])[CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4]1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 139598953-Aminomethyl-1-benzyl-4-chloropyrrolidine

Product 1

HCID 139130083-Acetylaminomethyl-1-benzyl-4-chloropyrrolidineYield 78.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 3-aminomethyl-1-benzyl-4-chloropyrrolidine (2.69 g) is added ethanol (50 ml) and thereto is added dropwise acetyl chloride (1.02 g) with stirring under ice-cooling. The mixture is stirred at room temperature overnight, then concentrated, neutralized with saturated aqueous sodium hydrogen carbonate, and extructed with dichloromethane. The dichloromethane layer is dried and concentrated to give 3-acetylaminomethyl-1-benzyl-4-chloropyrrolidine (2.50 g) as an yellow oil.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred at room temperature overnight
  3. concentrationconcentrated
  4. dry with materialThe dichloromethane layer is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ada00a0e55684e659624752873a26ccc
Source dataset
uspto-grants-1988_11
Patent number
US04786649

Reaction notes

Loading…