Hydrochloride 4-(8-phenyl-1,4-dioxaspiro[4,5]dec-8-yl)pyrrolidine hydrochloride → 4-Pyrrolidin-4-yl-4-phenylcyclohexanone

HRID 2422392Notes

Reaction equation

HRID 2422392 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>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 67244629Hydrochloride 4-(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

The hydrochloride 4-(8-phenyl-1,4-dioxaspiro[4,5]dec-8-yl)pyrrolidine hydrochloride (5.8 g, 17.9 mmol) was dissolved in 7.5N hydrochloric acid (16 ml) and stirred for 24 h at room temperature. On completion of hydrolysis the reaction mixture was extracted with diethyl ether (2×50 ml), the aqueous phase was made alkaline using 5N sodium hydroxide solution with ice cooling, extracted with dichloromethane (3×50 ml) and concentrated to small volume. The ketone 4-pyrrolidin-4-yl-4-phenylcyclohexanone was able to be isolated as a yellow solid with a melting point of 75-79° C. and a yield of 96% (4.1 g).

Workup

  1. customOn completion of hydrolysis the reaction mixture
  2. extractionwas extracted with diethyl ether (2×50 ml)
  3. extractionextracted with dichloromethane (3×50 ml)
  4. concentrationconcentrated to small volume
  5. customto be isolated as a yellow solid with a melting point of 75-79° C.

Sources & evidence

ORD record
ord-59364ef0a3f6451696ae3afac7d15b43
Source dataset
uspto-grants-2011_06
Patent number
US07960404B2

Reaction notes

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