Ethanol → HCID 67154696, compound

HRID 83083Notes

Reaction equation

HRID 83083 reaction equation
C([N:14]1[CH2:17][CH:16]([C:18]2[O:19][C:20]3[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=3[C:22]=2[CH3:23])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl:28]C(OC(Cl)C)=O.CCO>C(Cl)Cl>[ClH:28].[CH3:23][C:22]1[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[O:19][C:18]=1[CH:16]1[CH2:15][NH:14][CH2:17]1

Participants

5

Reactant 3

HCID 702EthanolHCID 5213051-Chloroethyl chloroformateHCID 671546541-Benzhydryl-3-(3-methylbenzofuran-2-yl)azetidine

Product 1

HCID 67154696HCID 67154696, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 1-benzhydryl-3-(3-methylbenzofuran-2-yl)azetidine (52.0 mg, 0.147 mmol) in DCM (4 mL) under N2 was added 1-chloroethyl chloroformate (18.0 μL, 0.167 mmol) and the reaction was stirred at rt under N2 for 4 h. Next, EtOH was added and the mixture was stirred under nitrogen at 50° C. for 21 h. The mixture was concentrated in vacuo and the residue triturated with Et2O (3×5 mL), yielding the title product (20.4 mg, 62%) as an off-white solid.

Workup

  1. stirringthe mixture was stirred under nitrogen at 50° C. for 21 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue triturated with Et2O (3×5 mL)

Sources & evidence

ORD record
ord-a977df717deb41048c716c8ffdb6fad0
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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