Methanol → HCID 19366964, compound

HRID 849557Notes

Reaction equation

HRID 849557 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:16][CH2:15][C:8]3([CH2:13][CH2:12][N:11](C)[CH2:10][CH2:9]3)[C:6]=2[CH:7]=1.[Cl:17]C(OCCCl)=O.CO>ClCCCl>[ClH:17].[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:16][CH2:15][C:8]3([CH2:9][CH2:10][NH:11][CH2:12][CH2:13]3)[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 123052-Chloroethyl chloroformateHCID 19366983HCID 19366983, compound

Product 1

HCID 19366964HCID 19366964, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5-fluoro-1'-methyl-spiro(2,3-dihydrobenzofuran-3,4'-piperidine) (1.21 g, 5.48 mmol) in 1,2-dichloroethane (12 mL) at room temp was treated with 2-chloroethyl chloroformate (1 mL, 9 mmol). A white precipitate formed, and the reaction was refluxed 2 h. MeOH (12 mL) was added and refluxing was continued for 2 h. The reaction was concentrated to a crude solid, which was triturated with EtOAc (5 mL) and filtered to yield 1.27 g (95%) of the title compound as a white crystalline solid.

Workup

  1. customA white precipitate formed
  2. temperaturethe reaction was refluxed 2 h
  3. temperaturerefluxing
  4. concentrationThe reaction was concentrated to a crude solid, which
  5. customwas triturated with EtOAc (5 mL)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-5d57c0d083664699b73716a27932e22d
Source dataset
uspto-grants-2000_01
Patent number
US06013652

Reaction notes

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