Water → HCID 23312235, compound

HRID 2057416Notes

Reaction equation

HRID 2057416 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 2 N 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 2 N 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-1483c07a57ac4e80a1db2caf2ae690ae
Source dataset
uspto-grants-1980_07
Patent number
US04210655

Reaction notes

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