Potassium Carbonate → HCID 20394259, compound

HRID 261500Notes

Reaction equation

HRID 261500 reaction equation
[CH:1]1([C:5](Cl)=[O:6])[CH2:4][CH2:3][CH2:2]1.[NH:8]1[CH2:13][CH2:12][C:11]2([CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH:1]1([C:5]([N:8]2[CH2:13][CH2:12][C:11]3([CH2:17][C:16]4[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=4[O:14]3)[CH2:10][CH2:9]2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78705Cyclobutanecarbonyl chlorideHCID 127332303H-Spiro(1-benzofuran-2,4'-piperidine)

Product 1

HCID 20394259HCID 20394259, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of 4.2 g of cyclobutylcarbonyl chloride in 10 ml of chloroform is added dropwise to a stirred mixture of 6.0 g of 2,3-dihydrospiro[benzofuran-2,4'-piperidine], Example 7, and 20.0 g of potassium carbonate in 75 ml of chloroform. After total addition, the reaction mixture is successively refluxed for 24 hours, cooled, filtered and poured into water. The biphasic mixture is sequentially washed with 3 N hydrochloric acid, 3 N sodium hydroxide, a saturated sodium chloride solution, dried and the solvent is removed, leaving a solid residue. The residue is recrystallized twice from a benzene-hexane mixture to give the product, 2,3-dihydro-1'-cyclobutylcarbonylspiro[benzofuran-2,4'-piperidine], mp 91°-93° C.

Workup

  1. additionAfter total addition
  2. temperaturethe reaction mixture is successively refluxed for 24 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. additionpoured into water
  6. washThe biphasic mixture is sequentially washed with 3 N hydrochloric acid, 3 N sodium hydroxide
  7. dry with materiala saturated sodium chloride solution, dried
  8. customthe solvent is removed
  9. customleaving a solid residue
  10. customThe residue is recrystallized twice from a benzene-hexane mixture

Sources & evidence

ORD record
ord-4151337cab7e4ca68108b79b6754199f
Source dataset
uspto-grants-1979_08
Patent number
US04166119

Reaction notes

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