Potassium Carbonate → HCID 21506805, compound

HRID 1287898Notes

Reaction equation

HRID 1287898 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][O:7]2)[CH2:3][CH2:2]1.C1O[C:18]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)([CH:19](Cl)[CH2:20][CH3:21])[O:17]C1.C(=O)([O-])[O-:32].[K+].[K+]>C(O)CCC>[F:29][C:26]1[CH:25]=[CH:24][C:23]([C:18]([CH2:19][CH2:20][CH2:21][N:1]2[CH2:6][CH2:5][C:4]3([C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:8](=[O:32])[O:7]3)[CH2:3][CH2:2]2)=[O:17])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 104424983H-spiro[2-benzofuran-1,4'-piperidine]HCID 23193548HCID 23193548, compound

Product 1

HCID 21506805HCID 21506805, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4.0 g. of 1,3-dihydrospiro[isobenzofuran-1,4'-piperidine], 6.04 g. of α-chloro-p-fluorobutyrophenone ethylene ketal, 10 g. of potassium carbonate, and 50 ml. of 1-butanol is heated under reflux with stirring for 65 hours, cooled, and filtered. The filtrate is concentrated to an oil which is dissolved in 50 ml. of ethanol and 50 ml. of 3N hydrochloric acid. After 2 hours, the solution is made basic and extracted with benzene. Concentration of the benzene solution provides 1,3-dihydro1'-[3-(4-fluorobenzoyl)propyl]spiro[isobenzofuran-1,4'-piperidine]-3-one as an oil; hydrochloride salt, m.p. 183°-184°.

Workup

  1. additionA mixture of 4.0 g
  2. temperatureunder reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated to an oil which
  6. dissolutionis dissolved in 50 ml
  7. waitAfter 2 hours
  8. extractionextracted with benzene

Sources & evidence

ORD record
ord-fe7ccccbc242499aba1281806e0a249b
Source dataset
uspto-grants-1976_10
Patent number
US03985889

Reaction notes

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