1-Chloroethyl chloroformate → 3-(3,4-Dichlorophenoxy)azetidine--hydrogen chloride (1/1)

HRID 1182112Notes

Reaction equation

HRID 1182112 reaction equation
C([N:14]1[CH2:17][CH:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>ClCCl>[ClH:25].[Cl:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[Cl:25])[O:18][CH:16]1[CH2:15][NH:14][CH2:17]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 150422273-(3,4-Dichlorophenoxy)-1-(diphenylmethyl)azetidine

Product 1

HCID 534397673-(3,4-Dichlorophenoxy)azetidine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-Benzhydryl-3-(3,4-dichloro-phenoxy)-azetidine (2.14 g, 6.4 mmol) in dry dichloromethane (20 ml) is treated with 1-chloroethylchloroformate (0.832 ml, 7.7 mmol) with stirring for 4 hours. The solvent is evaporated and the residue dissolved in methanol and refluxed for 18 hrs. The methanol is evaporated to a saturated solution, and then treated with diethylether. The resulting precipitate is filtered and dried under vacuum to afford 3-(3,4-Dichloro-phenoxy)-azetidine hydrochloride. 1H NMR (D6 DMSO, 400 Mhz) δ 9.5 (2H, brS), 7.6 (1H, d), 7.2 (1H, s), 6.9 (1H, d), 5.1 (1H, m), 4.4 (2H, m), 3.95 (2H, m).

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue dissolved in methanol
  3. temperaturerefluxed for 18 hrs
  4. customThe methanol is evaporated to a saturated solution
  5. additiontreated with diethylether
  6. filtrationThe resulting precipitate is filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-7854da69159f4ca6a4b0701071fcb5fe
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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