Water → HCID 23312235, compound

HRID 745814Notes

Reaction equation

HRID 745814 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][CH:9]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=4[CH:16]=3)[CH2:8][CH2:7]2)=O)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH:1]1([CH2:4][N:6]2[CH2:11][CH2:10][CH:9]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=4[CH:16]=3)[CH2:8][CH2:7]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 23312286HCID 23312286, compound

Product 1

HCID 23312235HCID 23312235, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 14.5 g of 1-(cyclopropylcarbonyl)-4-(2-benzofuranyl)-piperidine in 100 ml of tetrahydrofuran is added dropwise to a refluxing solution of 13.5 g of lithium aluminium hydride in 200 ml of tetrahydrofuran. After 15 hours' refluxing, the reaction mixture is cooled, and the excess lithium aluminium hydride broken down at -10° by means of 15 ml of water, 15 ml of 10% sodium hydroxide solution and 45 ml of water. The reaction solution is filtered off under suction and the filter residue subsequently washed with 1 liter of chloroform; the combined filtrates are then concentrated in vacuo. The residue is dissolved in 500 ml of 2N hydrochloric acid, and the acid solution washed with ether. The aqueous solution is thereupon adjusted by addition of 10% sodium hydroxide solution to pH 12, and extracted with 1 liter of chloroform. The chloroform solution is dried with sodium sulphate, filtered off with suction, and concentrated by evaporation to obtain crude 1 -(cyclopropylmethyl)-4-(2-benzofuranyl)-piperidine. After recrystallisation from hexane, the free base melts at 68°. The hydrochloride is prepared with hydrogen chloride in ethyl acetate, and recrystallised from ethyl acetate, whereupon it melts at 223°-225°.

Workup

  1. temperatureAfter 15 hours' refluxing
  2. temperaturethe reaction mixture is cooled
  3. filtrationThe reaction solution is filtered off under suction
  4. washthe filter residue subsequently washed with 1 liter of chloroform
  5. concentrationthe combined filtrates are then concentrated in vacuo
  6. dissolutionThe residue is dissolved in 500 ml of 2N hydrochloric acid
  7. washthe acid solution washed with ether
  8. additionThe aqueous solution is thereupon adjusted by addition of 10% sodium hydroxide solution to pH 12
  9. extractionextracted with 1 liter of chloroform
  10. dry with materialThe chloroform solution is dried with sodium sulphate
  11. filtrationfiltered off with suction
  12. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-e2a37c34d10f427b95be05dec6811cb8
Source dataset
uspto-grants-1986_07
Patent number
US04600719

Reaction notes

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