p-Toluenesulfonic acid monohydrate → 1-Benzyl-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine

HRID 431261Notes

Reaction equation

HRID 431261 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)=[CH:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 100395771-Benzyl-4-(4-fluorophenyl)piperidin-4-ol

Product 1

HCID 100615101-Benzyl-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

After weighing 80 g (0.28 mol) of 1-benzyl-4-(4-fluorophenyl)-4-hydroxypiperidine and 69.0 g (0.364 mol) of p-toluenesulfonic acid monohydrate to 400 ml of chlorobenzene under stirring, the reaction mixture is boiled under reflux for 3 hours while distilling out water introduced as crystal water and the water formed in the reaction. After termination of the reaction, 100 ml of chlorobenzene are additionally distilled out under atmospheric pressure. After cooling the mixture obtained to 0° C., the precipitated title product is filtered, twice washed with 10 ml of cold acetone each and dried on the air to give a yield of 90.5 g (73%), m.p.: 180-182° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. distillationwhile distilling out water
  3. additionintroduced as crystal water
  4. customthe water formed in the reaction
  5. distillationare additionally distilled out under atmospheric pressure
  6. temperatureAfter cooling the mixture
  7. customobtained to 0° C.
  8. customthe precipitated title product
  9. filtrationis filtered
  10. washtwice washed with 10 ml of cold acetone each and
  11. customdried on the air
  12. customto give a yield of 90.5 g (73%), m.p.: 180-182° C.

Sources & evidence

ORD record
ord-5468f00972be45758935635a62ca056d
Source dataset
uspto-grants-2003_12
Patent number
US06657062B1

Reaction notes

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