1-Chloroethyl chloroformate → 3-(4,4'-Dichlorobenzhydryloxy)azetidine

HRID 1785636Notes

Reaction equation

HRID 1785636 reaction equation
C([N:14]1[CH2:17][CH:16]([O:18][CH:19]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>ClCCl>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([CH:19]([O:18][CH:16]2[CH2:17][NH:14][CH2:15]2)[C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 689032041-Benzhydryl-3-(4,4'-dichlorobenzhydryloxy)azetidine

Product 1

HCID 689061393-(4,4'-Dichlorobenzhydryloxy)azetidineYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-benzhydryl-3-(4,4′-dichlorobenzhydryloxy)azetidine (35) (8.4 mmol) in dichloromethane (50 mL) was added 1-chloroethylchloroformate (16.9 mmol) dropwise at 0° C. and the reaction mixture was stirred at reflux for 6 hours. The reaction mixture was cooled to room temperature, concentrated in vacuo, then dissolved in methanol (50 mL) and stirred at room temperature for overnight. The reaction mixture was reduced in vacuo and triturated with diethyl ether (100 mL) to afford the desired product as a white solid (2.16 g, 74%).

Workup

  1. temperatureat reflux for 6 hours
  2. concentrationconcentrated in vacuo
  3. dissolutiondissolved in methanol (50 mL)
  4. stirringstirred at room temperature for overnight
  5. customtriturated with diethyl ether (100 mL)

Sources & evidence

ORD record
ord-4a37d7ea76d24ecaac385eef012c4fbe
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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