Acetonitrile → p-Chloro-n-propylbenzylamine

HRID 1730025Notes

Reaction equation

HRID 1730025 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.C(#N)C.[CH2:13]([NH2:16])[CH2:14][CH3:15].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:16][CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 7852PropylamineHCID 14798Sodium Hydroxide

Product 1

HCID 580714p-Chloro-n-propylbenzylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 48.3 g. 4-chlorobenzyl chloride in 40 ml. acetonitrile was added to a mixture of 18 g. propylamine, 12.6 g. sodium hydroxide, 50 ml. acetonitrile and 30 ml. water. The mixture was shaken intermittently for 45 minutes. An exothermic reaction occurred and a white solid separated in the lower phase. After a period of 4 days the reaction mixture was poured into a liter of water and the organic phase isolated with ether. Distillation of the ethereal extract gave an oily product N-4-chlorobenzyl-N-propylamine, b.p. 101°-106° C./1.7-2.5 mm. Hg.

Workup

  1. customAn exothermic reaction
  2. customa white solid separated in the lower phase
  3. additionAfter a period of 4 days the reaction mixture was poured into a liter of water
  4. customthe organic phase isolated with ether
  5. distillationDistillation of the ethereal
  6. extractionextract

Sources & evidence

ORD record
ord-c0fe75a6ac47414484e81e21bd332b5d
Source dataset
uspto-grants-1976_11
Patent number
US03991071

Reaction notes

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