Ethanol → HCID 67154551, compound

HRID 634018Notes

Reaction equation

HRID 634018 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([C:25]2[O:26][C:27]3[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=3[CH:29]=2)[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>ClCCl>[ClH:1].[O:26]1[C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[CH:29]=[C:25]1[CH:23]1[CH2:22][NH:21][CH2:24]1

Participants

5

Reactant 3

HCID 702EthanolHCID 5213051-Chloroethyl chloroformateHCID 671547231-Benzhydryl-3-(benzofuran-2-yl)azetidine

Product 1

HCID 67154551HCID 67154551, compoundYield 123%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-Chloroethyl chloroformate (36 μL, 0.33 mmol) was added to a solution of 1-benzhydryl-3-(benzofuran-2-yl)azetidine (108 mg, 0.32 mmol) in dichloromethane (3 mL) at 0° C. The reaction mixture was stirred for 2 hours at 0° C. and for 1 hour at room temperature. Ethanol (3 mL) was added at 0° C. and the reaction mixture was stirred for 2 hours at 0° C., for 19 hours at room temperature and for 4 hours at 40° C. After concentration to dryness, the crude mixture was triturated in n-pentane (2×4 mL) to afford the title compound as a pink solid (82 mg, 123%) which was used without further purification.

Workup

  1. stirringthe reaction mixture was stirred for 2 hours at 0° C., for 19 hours at room temperature and for 4 hours at 40° C
  2. concentrationAfter concentration to dryness
  3. customthe crude mixture was triturated in n-pentane (2×4 mL)

Sources & evidence

ORD record
ord-f155279175df4c7d8c59088a4b9e3b62
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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