4-(4-Bromophenyl)-4-hydroxypiperidine → 4-(4-Bromophenyl)-5,6-dihydropyridine

HRID 2383590Notes

Reaction equation

HRID 2383590 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 939114-(4-Bromophenyl)-4-hydroxypiperidine

Product 1

HCID 667303604-(4-Bromophenyl)-5,6-dihydropyridine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(4-bromophenyl)piperidin-4-ol (500 mg, 1.95 mmol) in TFA (4 mL) was heated to 90° C. for 2 h. The crude reaction mixture was concentrated under reduced pressure to dryness, to give a yellow solid (460 mg, used without further purification). MS ESI 237.9 [M+H]+, calcd for [C11H12BrN+H]+ 238.02.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under reduced pressure to dryness
  3. customto give
  4. customa yellow solid (460 mg, used without further purification)

Sources & evidence

ORD record
ord-2e1a7dbbead94791815212ba8de2dd59
Source dataset
uspto-grants-2012_09
Patent number
US08263596B2

Reaction notes

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