Water → 79601-34-6

HRID 2108202Notes

Reaction equation

HRID 2108202 reaction equation
Br.[CH2:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[CH2:6]1)[CH2:3][CH3:4].CC(C)([O-])C.[K+].[CH2:24]([Cl:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>C(O)(C)(C)C>[ClH:31].[CH2:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:12]=2)[CH2:6]1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 2304564779412-27-4HCID 23665647Potassium tert-butoxide

Product 1

HCID 7005449379601-34-6Yield 52.6%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of N-n-propyl-3-(3-hydroxyphenyl)piperidine hydrobromide (1.0 g. 0.0033 mol), potassium t-butoxide (1.0 g, 0.009 mol) and benzylchloride (1.0 g, 0.009 mol) in t-butanol (25 ml) was refluxed for 1 h. Water was added and the mixture extracted with ether. The organic phase was dried with Na2SO4 and evaporated to dryness giving a pale yellow oily residue. The residue was chromatographed through a silica gel column with methanol as eluant. The pertinent fractions were collected and evaporated to dryness. The oily residue was dissolved in ether and HCl-saturated ether was added, giving white crystals. Evaporation and treatment of the residue with acetone gave 0.60 g (52%) of the desired product as white crystals, mp. 171° C.

Workup

  1. temperaturewas refluxed for 1 h
  2. extractionthe mixture extracted with ether
  3. dry with materialThe organic phase was dried with Na2SO4
  4. customevaporated to dryness
  5. customgiving a pale yellow oily residue
  6. customThe residue was chromatographed through a silica gel column with methanol as eluant
  7. customThe pertinent fractions were collected
  8. customevaporated to dryness
  9. dissolutionThe oily residue was dissolved in ether
  10. additionHCl-saturated ether was added
  11. customgiving white crystals
  12. customEvaporation and treatment of the residue with acetone

Sources & evidence

ORD record
ord-42e4c8d2109e49b19dd7a5cce41a140d
Source dataset
uspto-grants-1990_06
Patent number
US04937346

Reaction notes

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