Ethanol → HCID 67154617, compound

HRID 634015Notes

Reaction equation

HRID 634015 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([C:25]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[O:27][CH:26]=2)[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>ClCCl>[ClH:1].[O:27]1[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:25]([CH:23]2[CH2:22][NH:21][CH2:24]2)=[CH:26]1

Participants

5

Reactant 3

HCID 702EthanolHCID 5213051-Chloroethyl chloroformate2×HCID 67154568HCID 67154568, compound

Product 1

HCID 67154617HCID 67154617, compoundYield 133.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-Chloroethyl chloroformate (18 μL, 0.16 mmol) was added to a solution of 1-benzhydryl-3-(benzofuran-3-yl)azetidine (52 mg, 0.15 mmol) in dichloromethane (1.5 mL) at 0° C. The reaction mixture was stirred for 15 minutes at 0° C. and for 4 hours at room temperature. An additional amount of 1-chloroethyl chloroformate (8 μL, 0.07 mmol) was added and stirring continued for 1 hour at room temperature. Ethanol (1.5 mL) was added and the reaction mixture was stirred for 3 days at room temperature. After concentration to dryness, the crude mixture was triturated in n-pentane (2×2 mL) to afford the title compound as a pink solid (42 mg, 130%) which was used without further purification.

Workup

  1. stirringstirring
  2. waitcontinued for 1 hour at room temperature
  3. stirringthe reaction mixture was stirred for 3 days at room temperature
  4. concentrationAfter concentration to dryness
  5. customthe crude mixture was triturated in n-pentane (2×2 mL)

Sources & evidence

ORD record
ord-c7b9c843e46841d09a36cf9a8e5edd8e
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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