1-Chloroethyl chloroformate → 3-(2,4'-Dichlorobenzhydryloxy)azetidine hydrochloride

HRID 1785634Notes

Reaction equation

HRID 1785634 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][CH:23]=[CH:22][C:21]=2[Cl:26])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>ClCCl>[ClH:26].[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH:19]([O:18][CH:16]1[CH2:17][NH:14][CH2:15]1)[C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 68902439HCID 68902439, compound

Product 1

HCID 689023433-(2,4'-Dichlorobenzhydryloxy)azetidine hydrochlorideYield 154.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-benzhydryl-3-(2,4′-dichlorobenzhydryloxy)azetidine (8) (38 mmol) in dichloromethane (400 mL) was added 1-chloroethylchloroformate (94 mmol) dropwise at 0° C. and the reaction mixture stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, then dissolved in methanol (400 mL) and stirred at room temperature for 2 hours. The reaction mixture was reduced in vacuo and diluted with isohexane (20 mL), diisopropyl ether (200 mL) and methanol (30 mL). Upon stirring, a precipitate formed. Filtration afforded the desired product as a white solid (10.1 g, 77%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in methanol (400 mL)
  3. stirringstirred at room temperature for 2 hours
  4. additiondiluted with isohexane (20 mL), diisopropyl ether (200 mL) and methanol (30 mL)
  5. stirringUpon stirring
  6. customa precipitate formed
  7. filtrationFiltration

Sources & evidence

ORD record
ord-1ab1297454164a85bff1887573bddc30
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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