Water → 3-[4-(1,1-Dimethylethyl)phenyl]pyrrolidine

HRID 974179Notes

Reaction equation

HRID 974179 reaction equation
S(=O)(=O)(O)O.[C:6]1([CH:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:17][C:18](=[CH2:20])[CH3:19].O>C(Cl)(Cl)(Cl)Cl>[C:18]([C:9]1[CH:10]=[CH:11][C:6]([CH:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)=[CH:7][CH:8]=1)([CH3:20])([CH3:19])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 31467433-Phenylpyrrolidine

Product 1

HCID 144068163-[4-(1,1-Dimethylethyl)phenyl]pyrrolidineYield 33%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

98 g (1 mole) of concentrated sulfuric acid were added dropwise to 29.4 g (0.2 mole) of 3-phenylpyrrolidine in 400 ml of carbon tetrachloride at 0°-5° C. After 15 minutes, 15.2 g (0.27 mole) of isobutylene were passed in gaseous form, the mixture was stirred for 1 hour at 0°-5° C. and hydrolysis was carried out with 400 ml of water at 20° C. The organic phase was separated off and the aqueous phase was extracted with twice 100 ml of dichloromethane. Working up of the organic phases gave 42 g of a crude product, which was fractionated under reduced pressure to give 13.4 g (33%) of a colorless oil of boiling point 84°-87° C./0.5 mbar.

Workup

  1. customhydrolysis
  2. customThe organic phase was separated off
  3. extractionthe aqueous phase was extracted with twice 100 ml of dichloromethane
  4. customgave 42 g of a crude product, which

Sources & evidence

ORD record
ord-7a750acb501e4782ac7187188c2d8abe
Source dataset
uspto-grants-1991_11
Patent number
US05068245

Reaction notes

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