p-Toluenesulfonic acid → HCID 67507811, compound

HRID 1468187Notes

Reaction equation

HRID 1468187 reaction equation
[F:1][C:2]1([F:15])[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1CCCCC1>[F:1][C:2]1([F:15])[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][C:11]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:10][CH2:9]2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31268PyrrolidineHCID 67507911HCID 67507911, compound

Product 1

HCID 67507811HCID 67507811, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Heat a solution of 4-(4,4-difluoro-piperidin-1-yl)-cyclohexanone (1.93 g 8.88 mmol), pyrrolidine (0.89 mL, 10.7 mmol) and p-toluenesulfonic acid (1 crystal) in cyclohexane (50 mL) to reflux with a Dean-Stark trap for 7 h. Cool the solution and filter through a plug of cotton wool. Evaporate to give 2.31 g, 96% yield of 4,4-difluoro-1-(4-pyrrolidin-1-yl-cyclohex-3-enyl)-piperidine as an oil.

Workup

  1. temperatureto reflux with a Dean-Stark trap for 7 h
  2. temperatureCool the solution
  3. filtrationfilter through a plug of cotton wool
  4. customEvaporate

Sources & evidence

ORD record
ord-e5f0d27826164d26a9dbc051f14b7185
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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