Tert-Butylamine → 3-Benzyloxy-1-(tert.butyl)azetidine

HRID 2198853Notes

Reaction equation

HRID 2198853 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.[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>O>[CH2:1]([O:8][CH:9]1[CH2:12][N:18]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 5155009Benzene, [[2-chloro-1-(chloromethyl)ethoxy]methyl]-

Product 1

HCID 205173323-Benzyloxy-1-(tert.butyl)azetidineYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

21.9 Parts of 2-benzyloxy-1,3-dichloro-propane, 71.3 parts of tert.-butylamine and 50 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, 17.5 parts of 3-benzyloxy-1-(tert.-butyl)azetidine boiling at 94°-96° C. under 2 mm Hg were obtained. The yield was 80%. The results of infra-red spectrum analysis and nuclear magnetic resonance analysis 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-fd49a4d277ac40b7bcf1fcde0816fe07
Source dataset
uspto-grants-1982_11
Patent number
US04360464

Reaction notes

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