Ammonia → 1-(Aminomethyl)-4-propylpyrrolidin-2-one

HRID 1896380Notes

Reaction equation

HRID 1896380 reaction equation
Cl[CH2:2][N:3]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]1=[O:11].[NH3:12]>C1(C)C=CC=CC=1>[NH2:12][CH2:2][N:3]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]1=[O:11]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 536292161-(Chloromethyl)-4-propylpyrrolidin-2-one

Product 1

HCID 536292181-(Aminomethyl)-4-propylpyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(chloromethyl)-4-propylpyrrolidin-2-one x63 (41.34 g, 0.235 mol) in toluene (350 ml) is added dropwise at −78° C. to liquid ammonia (300 ml). At the end of the addition, the temperature is raised slowly to room temperature, and ammonia of the crude mixture is allowed to distill at room temperature overnight. Filtration of the reaction mixture and subsequent evaporation lead to 55 g of the crude 1-(aminomethyl)-4-propylpyrrolidin-2-one x76 which is used without further purification.

Workup

  1. additionAt the end of the addition
  2. distillationto distill at room temperature overnight
  3. filtrationFiltration of the reaction mixture and subsequent evaporation lead to 55 g of the crude 1-(aminomethyl)-4-propylpyrrolidin-2-one x76 which
  4. customis used without further purification

Sources & evidence

ORD record
ord-074e5cebe0054f61a821410da7743c6c
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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