Water → HCID 23312241, compound

HRID 745815Notes

Reaction equation

HRID 745815 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[C:6]([N:8]1[CH2:13][CH2:12][CH:11](C2OC3C=CC=CC=3C=2)[CH2:10][CH2:9]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[O:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[CH2:6][N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[C:38]1[O:37][C:41]2[CH:24]=[CH:25][CH:3]=[CH:4][C:40]=2[CH:39]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydride2×HCID 23312246HCID 23312246, compound

Product 1

HCID 23312241HCID 23312241, compound

Procedure

A solution of 27.6 g of 1-(3,4,5-trimethoxybenzoyl)-4-(2-benzofuranyl)-piperidine in 150 ml of tetrahydrofuran is added dropwise to a refluxing solution of 4.0 g of lithium aluminium hydride in 120 ml of tetrahydrofuran. After 4 hours' refluxing, the reaction mixture is cooled, and the excess lithium aluminium hydride decomposed at -10° by means of 4 ml of water. The reaction solution is filtered off under suction, the filter residue then washed with 1 liter of chloroform, and the combined filtrates concentrated in vacuo. The residue is dissolved in 500 ml of 10% aqueous methanesulphonic acid, and the acid solution washed with ether. The aqueous phase is thereupon adjusted to pH 12 by addition of 30% sodium hydroxide solution, and extracted with 1 liter of chloroform. The chloroform solution is dried with sodium sulphate, filtered, and concentrated by evaporation to obtain crude 1-(3,4,5-trimethoxybenzyl)-2-(2-benzofuranyl)-piperidine. The hydrochloride is prepared with hydrogen chloride in ethyl acetate, and recrystallised from ethyl acetate, whereupon it melts at 212°.

Workup

  1. temperatureAfter 4 hours' refluxing
  2. temperaturethe reaction mixture is cooled
  3. filtrationThe reaction solution is filtered off under suction
  4. washthe filter residue then washed with 1 liter of chloroform
  5. concentrationthe combined filtrates concentrated in vacuo
  6. dissolutionThe residue is dissolved in 500 ml of 10% aqueous methanesulphonic acid
  7. washthe acid solution washed with ether
  8. additionThe aqueous phase is thereupon adjusted to pH 12 by addition of 30% sodium hydroxide solution
  9. extractionextracted with 1 liter of chloroform
  10. dry with materialThe chloroform solution is dried with sodium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-cfcc2493bc4f42e791c37034c46e49dc
Source dataset
uspto-grants-1986_07
Patent number
US04600719

Reaction notes

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