Potassium Carbonate → HCID 21506804, compound

HRID 1287897Notes

Reaction equation

HRID 1287897 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)[C:8](=[O:15])[O:7]2)[CH2:3][CH2:2]1.Cl[CH2:17][CH2:18][CH2:19][CH:20]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[F:27][C:24]1[CH:23]=[CH:22][C:21]([CH:20]([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)[CH2:19][CH2:18][CH2:17][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:15])[O:7]3)[CH2:3][CH2:2]2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 98342553H-spiro(isobenzofuran-1,4'-piperidin)-3-one

Product 1

HCID 21506804HCID 21506804, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4.0 g. of 1,3-dihydrospiro[isobenzofuran-1,4'-piperidine]-3-one, 6.4 g. of 4-chloro1,1-di(4-fluorophenyl)butane, 10 g. of potassium carbonate, and 25 ml. of 1-butanol is heated under reflux for 48 hours and filtered. The filtrate is diluted with water and extracted with benzene. The benzene solution is dried over potassium carbonate and concentrated to an oil, 1,3-dihydro-1'-[4,4-di(4-fluorophenyl)butyl]spiro[isobenzofuran-1,4'-piperidine]-3-one. The oil is converted to a crystalline hydrochloride salt, m.p. 182°-183° (from benzene).

Workup

  1. additionA mixture of 4.0 g
  2. temperatureunder reflux for 48 hours
  3. filtrationfiltered
  4. additionThe filtrate is diluted with water
  5. extractionextracted with benzene
  6. dry with materialThe benzene solution is dried over potassium carbonate
  7. concentrationconcentrated to an oil, 1,3-dihydro-1'-[4,4-di(4-fluorophenyl)butyl]spiro[isobenzofuran-1,4'-piperidine]-3-one

Sources & evidence

ORD record
ord-52435a7324c24920ad016da2f097483f
Source dataset
uspto-grants-1976_10
Patent number
US03985889

Reaction notes

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