1-Chloroethyl chloroformate → 3H-Spiro[1-benzofuran-2,3'-piperidine]

HRID 1781365Notes

Reaction equation

HRID 1781365 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][C:10]2([CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>ClC(Cl)C>[NH:8]1[CH2:13][CH2:12][CH2:11][C:10]2([CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 19045403HCID 19045403, compound

Product 1

HCID 190452923H-Spiro[1-benzofuran-2,3'-piperidine]Yield 94.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 13 g (46 mmole) of 1'-benzyl-2,3-dihydrospiro(benzofuran-2,3'-piperidine) in 100 mL dichloroethane was treated with 7.31 g (5.2 mL, 51 mmoles) of 1-chloroethylchloroformate at room temperature for 1/2 hour. The reaction mixture was concentrated and the residue dissolved in CH3OH and heated to reflux for 1/2 hour. The methanol was evaporated at reduced pressure, and the residue partitioned between ethyl acetate and 1 N HCl. The ethyl acetate layer was discarded and the aqueous phase was basified to pH 9 and reextracted with ethyl acetate. The ethyl acetate solution was dried over magnesium sulfate, filtered and concentrated in vacuo to give 8.2 g product.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in CH3OH
  3. temperatureheated
  4. temperatureto reflux for 1/2 hour
  5. customThe methanol was evaporated at reduced pressure
  6. customthe residue partitioned between ethyl acetate and 1 N HCl
  7. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-497ce0dac18148448d14e82b382fc215
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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