Sodium borohydride → HCID 23312350, compound

HRID 745823Notes

Reaction equation

HRID 745823 reaction equation
[BH4-].[Na+].[I-].[CH3:4][NH+:5]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[CH:15]=2)[CH2:6]1>O.CO>[CH3:4][N:5]1[CH2:10][CH:9]=[CH:8][CH:7]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[CH:15]=2)[CH2:6]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 23312370HCID 23312370, compound

Product 1

HCID 23312350HCID 23312350, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 50 g of sodium borohydride in 100 ml of water is added dropwise, with stirring and external cooling, to a solution of 56.0 g of 1-methyl-3-(2-benzofuranyl)-piperidinium-iodide in 600 ml of methanol, the manner of addition being such that the reaction temperature does not exceed 35°. The solution is subsequently stirred for 15 hours at room temperature and again a solution of 50 g of sodium borohydride in 100 ml of water is added dropwise at a temperature not exceeding 35°. The methanol is thereupon evaporated off in vacuo; the aqueous phase remaining behind is extracted twice with 300 ml of chloroform each time, the chloroform solution dried over sodium sulphate, filtered, and concentrated by evaporation. The 1-methyl-3-(2-benzofuranyl)-1,2,3,6-tetrahydropyridine obtained is recrystallised from di-isopropylether, and then melts at 63°. The hydrochloride prepared therefrom with a solution of hydrogen chloride in ethyl acetate melts, after recrystallisation from ethyl acetate, at 244°-246°.

Workup

  1. customdoes not exceed 35°
  2. stirringThe solution is subsequently stirred for 15 hours at room temperature
  3. customexceeding 35°
  4. customThe methanol is thereupon evaporated off in vacuo
  5. extractionthe aqueous phase remaining behind is extracted twice with 300 ml of chloroform each time
  6. dry with materialthe chloroform solution dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c919aeba711b416d901edbaffc92d8fb
Source dataset
uspto-grants-1986_07
Patent number
US04600719

Reaction notes

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