Sodium borohydride → HCID 23312196, compound

HRID 745817Notes

Reaction equation

HRID 745817 reaction equation
[BH4-].[Na+].[I-].[CH3:4][N+:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:14]=3[CH:15]=2)=[CH:7][CH:6]=1>O.CO>[CH3:4][N:5]1[CH2:6][CH:7]=[C:8]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:14]=3[CH:15]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 23312242HCID 23312242, compound

Product 1

HCID 23312196HCID 23312196, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 70 g of sodium borohydride in 150 ml of water is added dropwise, with stirring and external cooling, to a solution of 70 g of 1-methyl-4-(5-chloro-2-benzofuranyl)-pyridinium-iodide in 500 ml of methanol, the manner of addition being such that the reaction temperature does not exceed 35°. The solution is subsequently stirred for 20 hours at room temperature. The methanol is thereupon evaporated off in vacuo; the aqueous phase remaining behind is extracted twice with 500 ml of chloroform each time, the chloroform solution dried over sodium sulphate, filtered, and concentrated by evaporation. The 1-methyl-4-(5-chloro-2-benzofuranyl)-1,2,3,6-tetrahydropyridine obtained is recrystallised from hexane, and then melts at 108°-118°. The hydrochloride prepared therefrom with a solution of hydrogen chloride in ethyl acetate melts, after recrystallisation from ethyl acetate, at 266°.

Workup

  1. customdoes not exceed 35°
  2. stirringThe solution is subsequently stirred for 20 hours at room temperature
  3. customThe methanol is thereupon evaporated off in vacuo
  4. extractionthe aqueous phase remaining behind is extracted twice with 500 ml of chloroform each time
  5. dry with materialthe chloroform solution dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-63a279aa985549edacb800c41047375e
Source dataset
uspto-grants-1986_07
Patent number
US04600719

Reaction notes

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