2-Aminomethyl-1-ethylpyrrolidine → 5-chloro-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-4-methyl-benzamide

HRID 1077276Notes

Reaction equation

HRID 1077276 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH2:9])[CH3:2].[CH3:10][O:11][C:12]1[CH:20]=[C:19]([CH3:21])[C:18]([Cl:22])=[CH:17][C:13]=1[C:14](Cl)=[O:15]>CC(CC)=O>[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:14](=[O:15])[C:13]1[CH:17]=[C:18]([Cl:22])[C:19]([CH3:21])=[CH:20][C:12]=1[O:11][CH3:10])[CH3:2]

Participants

4

Reactant 2

HCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 215361405-Chloro-2-methoxy-4-methylbenzoyl chloride

Product 1

HCID 2067095-chloro-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-4-methyl-benzamideYield 101.9%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Conditions

Temperature
5 °C

Procedure

In a 1 liter flask equipped with an agitator, a thermometer and a dropping funnel, there are put 46 g (0.36 mole) of 1-ethyl-2-aminomethylpyrrolidine and 45 ml of methylethylketone. While maintaining the temperature of the mixture at about 5° C, there are added dropwise 79 g (0.36 mole) of 2-methoxy-4-methyl-5-chlorobenzoyl chloride dissolved in 400 ml of methylethylketone. The introduction requires about 1 hour. There is precipitation of N-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-4-methyl-5-chlorobenzamide hydrochloride which is drained, washed on a filter with methylethylketone and air-dried. There are obtained 114 g (yield 91%) of product in the form of white crystals (m.p. 162°-163° C).

Workup

  1. customIn a 1 liter flask equipped with an agitator
  2. customprecipitation of N-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-4-methyl-5-chlorobenzamide hydrochloride which
  3. washwashed on
  4. filtrationa filter with methylethylketone
  5. customair-dried

Sources & evidence

ORD record
ord-536e6f62053a4310bd47fd4557739602
Source dataset
uspto-grants-1976_05
Patent number
US03959477

Reaction notes

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