Hydrogen Bromide → HCID 12542653, compound

HRID 1733327Notes

Reaction equation

HRID 1733327 reaction equation
Cl.C[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:6][CH:5]=1.Br>O>[OH:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 12542652HCID 12542652, compound

Product 1

HCID 12542653HCID 12542653, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
157 °C

Procedure

A mixture of 3 g of 4-[α-(4-methoxyphenyl)-2-tolyl]piperidine hydrochloride, Example 39, and 48 ml of 48% HBr is refluxed on an oil bath (157° C.) with stirring for 32 minutes, cooled and then poured onto 48 ml of cooled water. The resulting suspension is quenched with 48 ml of concentrated ammonium hydroxide, stirred thoroughly and the solid is collected by suction filtration. The filter cake is dried in vacuo at 40° C. over sodium hydroxide pellets and then dissolved in 500 ml of hot absolute ethanol. 32 ml of triethylamine is added to the hot ethanolic solution. The hot solution is diluted with chloroform and then washed twice with water. The organic phase is collected, dried and filtered and then the solvent evaporated off leaving a solid product which is recrystallized from absolute ethanol in the presence of activated charcoal to give yellowish crystals, mp 217°-221° C. of 4-[α-(4-hydroxyphenyl)-2-tolyl]piperidine.

Workup

  1. temperaturecooled
  2. customThe resulting suspension is quenched with 48 ml of concentrated ammonium hydroxide
  3. stirringstirred thoroughly
  4. filtrationthe solid is collected by suction filtration
  5. dry with materialThe filter cake is dried in vacuo at 40° C. over sodium hydroxide pellets
  6. dissolutiondissolved in 500 ml of hot absolute ethanol
  7. addition32 ml of triethylamine is added to the hot ethanolic solution
  8. additionThe hot solution is diluted with chloroform
  9. washwashed twice with water
  10. customThe organic phase is collected
  11. customdried
  12. filtrationfiltered
  13. customthe solvent evaporated off
  14. customleaving a solid product which
  15. customis recrystallized from absolute ethanol in the presence of activated charcoal

Sources & evidence

ORD record
ord-25736393a98843d7aefa18a884601524
Source dataset
uspto-grants-1980_12
Patent number
US04241071

Reaction notes

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