Hydrochloric Acid → 1-Benzyl-4-(3-bromo-2-ethylphenyl)-1,2,3,6-tetrahydropyridine

HRID 1942683Notes

Reaction equation

HRID 1942683 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[C:16]=2[CH2:22][CH3:23])(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CC(O)=O>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[C:16]=2[CH2:22][CH3:23])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 584940321-Benzyl-4-(3-bromo-2-ethylphenyl)piperidin-4-ol

Product 1

HCID 584941291-Benzyl-4-(3-bromo-2-ethylphenyl)-1,2,3,6-tetrahydropyridineYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-benzyl-4-(3-bromo-2-ethyl-phenyl)-piperidin-4-ol (D116) (30 g, 80.15 mmol) in HOAc (300 mL) was added hydrochloric acid (45 mL, 37%). The reaction mixture was refluxed for 12 hr and concentrated in vacuo. The residue was purified by column chromatography to afford 1-benzyl-4-(3-bromo-2-ethyl-phenyl)-1,2,3,6-tetrahydro-pyridine (D117) (24 g). MS (ES): C20H22BrN requires 355. found 356 (M+H+).

Workup

  1. temperatureThe reaction mixture was refluxed for 12 hr
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-df16b7fc6bb04a5890212643ac852234
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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