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

HRID 1591161Notes

Reaction equation

HRID 1591161 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 7.13 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 1N 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 1N HCl
  7. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c021af7f8244d2787829aaacebc1f2c
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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