Methanol → Azetidine, 3-(p-chlorophenyl)-

HRID 2307218Notes

Reaction equation

HRID 2307218 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:11][N:10](C(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:9]2)=[CH:4][CH:3]=1.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.ClC(OC(Cl)C)=O.CO>ClCCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][NH:10][CH2:11]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 88675Proton spongeHCID 5213051-Chloroethyl chloroformateHCID 22605415HCID 22605415, compound

Product 1

HCID 23620Azetidine, 3-(p-chlorophenyl)-

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of compound 6 (0.36 g, 1.1 mmol) in 1,2-dichloroethane (10 mL) containing proton sponge (0.02 g), cooled in an ice-water bath under an argon atmosphere, was added dropwise 1-chloroethyl chloroformate (0.3 mL, 3.1 mmol). The resultant solution was boiled at reflux for 4 hours, cooled and was concentrated in vacuo. The residue obtained was mixed with methanol (10 mL) and heated under reflux for 2 hours, then cooled and concentrated in vacuo to give the hydrochloride salt of 3-(4-chlorophenyl)azetidine (7) which was used without further purification.

Workup

  1. temperaturecooled in an ice-water bath under an argon atmosphere
  2. temperatureat reflux for 4 hours
  3. temperaturecooled
  4. concentrationwas concentrated in vacuo
  5. customThe residue obtained
  6. temperatureheated
  7. temperatureunder reflux for 2 hours
  8. temperaturecooled
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef590181744a4e46bdcdc85ac895d40b
Source dataset
uspto-grants-2004_12
Patent number
US06831078B1

Reaction notes

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