Ethanol → HCID 67154656, compound

HRID 2172093Notes

Reaction equation

HRID 2172093 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([O:25][CH2:26][CH2:27][CH2:28][C:29]([F:32])([F:31])[F:30])[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>ClCCl>[ClH:1].[F:32][C:29]([F:30])([F:31])[CH2:28][CH2:27][CH2:26][O:25][CH:23]1[CH2:22][NH:21][CH2:24]1

Participants

5

Reactant 3

HCID 702EthanolHCID 5213051-Chloroethyl chloroformateHCID 671546911-Benzhydryl-3-(4,4,4-trifluorobutoxy)-azetidine

Product 1

HCID 67154656HCID 67154656, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloroethyl chloroformate (65 μL, 0.60 mmol) was added to a solution of 1-benzhydryl-3-(4,4,4-trifluorobutoxy)-azetidine (200 mg, 0.57 mmol) in dichloromethane (5 mL) at 0° C. The reaction mixture was stirred for 3 hours and 30 minutes at room temperature. Ethanol (5 mL) was then added and the mixture was stirred for an additional 2 hours at 0° C. and 2 hours at 70° C. The reaction mixture was concentrated under vacuum and the residue was triturated in petroleum ether (2×20 mL) to give a colorless oil (130 mg, quantitative) which was used without further purification.

Workup

  1. stirringthe mixture was stirred for an additional 2 hours at 0° C. and 2 hours at 70° C
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue was triturated in petroleum ether (2×20 mL)
  4. customto give a colorless oil (130 mg, quantitative) which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-7dbb4be8df1345a78fdadb8488911124
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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