Propylamine → 3-Benzyloxy-1-(n-propyl)azetidine

HRID 328900Notes

Reaction equation

HRID 328900 reaction equation
[CH2:1]([O:8][CH:9]([CH2:12]Cl)[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([NH2:17])[CH2:15][CH3:16]>O>[CH2:1]([O:8][CH:9]1[CH2:12][N:17]([CH2:14][CH2:15][CH3:16])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 5155009Benzene, [[2-chloro-1-(chloromethyl)ethoxy]methyl]-

Product 1

HCID 205173373-Benzyloxy-1-(n-propyl)azetidineYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

21.9 parts of 2-benzyloxy-1,3-dichloropropane, 59.1 parts of n-propylamine and 59.1 parts of water were added to an autoclave, and the mixture was heated at 90° C. for 48 hours with agitation. The reaction mixture was cooled and treated in the same manner as in Example 29, followed by distillation under reduced pressure. As a result 13.7 parts of 3-benzyloxy-1-(n-propyl)azetidine boiling at 101° - 103° C. under 2 mm Hg were obtained. The yield was 67%. The results of infra-red spectrum analysis and nuclear magnetic resonance analysis of the product are as follows:

Workup

  1. temperatureThe reaction mixture was cooled
  2. additiontreated in the same manner as in Example 29
  3. distillationfollowed by distillation under reduced pressure

Sources & evidence

ORD record
ord-c38c256c57644aef8f18d9dcbfef3ddb
Source dataset
uspto-grants-1977_04
Patent number
US04018824

Reaction notes

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