Hydrogen Bromide → 1,2-Benzenediol, 4-[1-(2-phenylethyl)-3-piperidinyl]-

HRID 616036Notes

Reaction equation

HRID 616036 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH:11]([C:15]3[CH:20]=[CH:19][C:18]([O:21]C)=[C:17]([O:23]C)[CH:16]=3)[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br>>[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH:11]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([OH:23])[CH:16]=3)[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 203708433-(3,4-Dimethoxyphenyl)-1-(2-phenylethyl)piperidine

Product 1

HCID 64543281,2-Benzenediol, 4-[1-(2-phenylethyl)-3-piperidinyl]-Yield 88.5%

Procedure

A mixture of 3.3 g of N-(β-phenylethyl)-3-(3',4'-dimethoxyphenyl)-piperidine and 33 ml of 66% hydrobromic acid was refluxed for an hour and was then distilled to dryness under reduced pressure. The residue was taken up in a water-methylene chloride mixture and was made alkaline with an aqueous solution saturated with sodium bicarbonate. The organic phase was decanted and the aqueous phase was extracted with methylene chloride. The combined organic phases were washed with water, dried over magnesium sulfate and distilled to dryness under reduced pressure to obtain 2.67 g of N-(β-phenylethyl)-3-(3',4'-dihydroxyphenyl)-piperidine.

Workup

  1. temperaturewas refluxed for an hour
  2. distillationwas then distilled to dryness under reduced pressure
  3. customThe organic phase was decanted
  4. extractionthe aqueous phase was extracted with methylene chloride
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationdistilled to dryness under reduced pressure

Sources & evidence

ORD record
ord-87a10f51aed242c8b13e038c9760f7e9
Source dataset
uspto-grants-1978_02
Patent number
US04072685

Reaction notes

Loading…