HCID 18956199, compound → HCID 18956196, compound

HRID 2379727Notes

Reaction equation

HRID 2379727 reaction equation
[ClH:1].C[O:3][C:4]1[CH:5]=[C:6]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1>Br>[ClH:1].[OH:3][C:4]1[CH:5]=[C:6]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 18956199HCID 18956199, compound

Product 1

HCID 18956196HCID 18956196, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

) 6.7 g 4-(3-methoxyphenyl)-1-(3-phenylpropyl)piperidine hydrochloride was refluxed with 80 ml 48% HBr for an hour. The products were cooled, the aqueous layer decanted and concentrated in vacuo. The resulting residue and insolubles were treated with excess saturated sodium bicarbonate and extracted with methylene chloride twice. The methylene chloride layer was washed twice with saturated bicarbonate and dried over magnesium sulfate and concentrated in vacuo. The resulting viscous oil was taken up in 50 ml acetone and HCl was added, resulting in precipitation. The precipitate was filtered off affording 8.6 g of crude product. The product was recrystallized from 110 ml absolute ethanol and 50 ml ether, yielding 4-(3-hydroxyphenyl)-1-(3-phenylpropyl)piperidine hydrochloride, melting point 211°-213° C.

Workup

  1. temperatureThe products were cooled
  2. customthe aqueous layer decanted
  3. concentrationconcentrated in vacuo
  4. additionThe resulting residue and insolubles were treated with excess saturated sodium bicarbonate
  5. extractionextracted with methylene chloride twice
  6. washThe methylene chloride layer was washed twice with saturated bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. additionHCl was added
  10. customresulting in precipitation
  11. filtrationThe precipitate was filtered off
  12. customaffording 8.6 g of crude product
  13. customThe product was recrystallized from 110 ml absolute ethanol and 50 ml ether

Sources & evidence

ORD record
ord-a68f8af17dd94f45a2f46e9423627fe8
Source dataset
uspto-grants-1994_11
Patent number
US05364867

Reaction notes

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