2-Chlorobenzyl chloride → 1-(2-Chlorobenzyl)pyrrolidine

HRID 27446

Reaction equation

HRID 27446 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 119062-Chlorobenzyl chlorideHCID 31268Pyrrolidine

Product 1

HCID 4094341-(2-Chlorobenzyl)pyrrolidineYield 75.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 50 g of 2-chlorobenzyl chloride in 100 ml of toluene is added in portions under agitation to a solution of 55 g of pyrrolidine in 150 ml of toluene, maintaining the temperature below 40° C. When all has been added, the mixture is brought to boiling point and heated under reflux for three hours. After cooling, it is washed twice with water, the toluene solution is dried over K2CO3, and the solvent is removed under reduced pressure. The residue is distilled under vacuum. B.P.=102°-104° C. 46 grams of N-(2-chlorobenzyl)-pyrrolidine are obtained. The analytical and spectral (I.R., N.M.R.) data agree with the proposed formula. Treating a solution in ether with gaseous HC1 gives the hydrochloride, M.P. 170° C.

Workup

  1. temperaturemaintaining the temperature below 40° C
  2. additionWhen all has been added
  3. temperatureheated
  4. temperatureunder reflux for three hours
  5. temperatureAfter cooling
  6. washit is washed twice with water
  7. dry with materialthe toluene solution is dried over K2CO3
  8. customthe solvent is removed under reduced pressure
  9. distillationThe residue is distilled under vacuum

Sources & evidence

ORD record
ord-03cbffd768e0474ab07b13ac4c1b5e32
Source dataset
uspto-grants-1980_09
Patent number
US04221805

Linked notes

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