alpha,alpha-Bis(3-methoxyphenyl)-4-piperidineethanol → 4-[2,2-Bis(3-methoxyphenyl)ethenyl]piperidine

HRID 1249586Notes

Reaction equation

HRID 1249586 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=2)(O)[CH2:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][CH:8]=1>FC(F)(F)C(O)=O>[CH3:25][O:24][C:20]1[CH:19]=[C:18]([C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 1

HCID 13754499alpha,alpha-Bis(3-methoxyphenyl)-4-piperidineethanol

Product 1

HCID 137545014-[2,2-Bis(3-methoxyphenyl)ethenyl]piperidineYield 90.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of alpha,alpha-bis(3-methoxyphenyl)-4-piperidine-ethanol (15 g) in trifluoroacetic acid (30 ml) was stirred at ambient temperature for one hour, then the solvent was removed in vacuo. The residue was partitioned between toluene (50 ml) and 1N sodium hydroxide (100 ml), and the separated aqueous layer was reextracted with toluene (20 ml). The combined toluene extracts were washed with 1N sodium hydroxide solution, then were dried over potassium carbonate and evaporated to give 12.8 g of 4-[2,2-bis(3-methoxyphenyl)ethenyl]piperidine as an oil.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between toluene (50 ml) and 1N sodium hydroxide (100 ml)
  3. washThe combined toluene extracts were washed with 1N sodium hydroxide solution
  4. dry with materialwere dried over potassium carbonate
  5. customevaporated

Sources & evidence

ORD record
ord-75360393f5b3463fa3fb2d8db2f696c3
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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