Sodium Carbonate → HCID 54334119, compound

HRID 1076881Notes

Reaction equation

HRID 1076881 reaction equation
[NH:1]1[CH2:5][CH2:4][C:3]2([C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]([OH:14])[CH2:6]2)[CH2:2]1.Cl[CH2:16][CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:19](=[O:20])[CH2:18][CH2:17][CH2:16][N:1]2[CH2:5][CH2:4][C:3]3([C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[CH:7]([OH:14])[CH2:6]3)[CH2:2]2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 215386612,3-Dihydrospiro[1H-indene-1,3′-pyrrolidin]-3-ol

Product 1

HCID 54334119HCID 54334119, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.5 g of spiro[indan-1,3'-pyrrolidin]-3-ol, 12.0 g of 4-chloro-p-fluorobutyrophenone and 11.5 g of sodium carbonate are heated at reflux in 100 cc of dimethyl formamide while stirring for 20 hours. After cooling, filtration is effected, the filtrate is evaporated to dryness, taken up in 300 cc of chloroform and extracted thrice with 50 cc amounts of 2 N hydrochloric acid. The acid extract is rendered alkaline with 2 N caustic soda solution while cooling and extraction is effected with chloroform. The crude title compound, obtained as oil after concentrating the chloroform phase by evaporation, is converted into the hydrogen fumarate with fumaric acid. The hydrogen fumarate of the title compound has a M.P. of 174°-176° (from ethanol/ether).

Workup

  1. temperatureAfter cooling
  2. filtrationfiltration
  3. customthe filtrate is evaporated to dryness
  4. extractionextracted thrice with 50 cc amounts of 2 N hydrochloric acid
  5. extractionThe acid extract
  6. temperaturewhile cooling
  7. extractionextraction

Sources & evidence

ORD record
ord-29d6482888544a3999248df08740c86d
Source dataset
uspto-grants-1976_05
Patent number
US03958003

Reaction notes

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