4-(8-Phenyl-1,4-dioxaspiro[4.5]dec-8-yl)pyrrolidine hydrochloride → 4-Pyrrolidin-4-yl-4-phenylcyclohexanone

HRID 1095482Notes

Reaction equation

HRID 1095482 reaction equation
Cl.[C:2]1([C:8]2([CH:18]3[CH2:22][NH:21][CH2:20][CH2:19]3)[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl>[NH:21]1[CH2:22][CH:18]([C:8]2([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)[CH2:19][CH2:20]1

Participants

3

Reactant 1

HCID 574751024-(8-Phenyl-1,4-dioxaspiro[4.5]dec-8-yl)pyrrolidine hydrochloride

Product 1

HCID 574751044-Pyrrolidin-4-yl-4-phenylcyclohexanoneYield 96%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-(8-Phenyl-1,4-dioxaspiro[4.5]dec-8-yl)pyrrolidine hydrochloride (5.8 g, 17.9 mmol) was dissolved in 7.5 N hydrochloric acid (16 ml) and the mixture was stirred at room temperature for 24 h. When the hydrolysis had ended, the reaction mixture was extracted with diethyl ether (2×50 ml), and the aqueous phase was rendered alkaline with 5 N sodium hydroxide solution, while cooling with ice, and extracted with methylene chloride (3×50 ml) and the extract was concentrated. It was possible to isolate the ketone Ket-8 as a yellow solid with a melting point of 75-79° C. and a yield of 96% (4.1 g).

Workup

  1. extractionthe reaction mixture was extracted with diethyl ether (2×50 ml)
  2. temperaturewhile cooling with ice
  3. extractionextracted with methylene chloride (3×50 ml)
  4. concentrationthe extract was concentrated

Sources & evidence

ORD record
ord-cc9448a2ede7496da8fdadb44a867ece
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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