Sodium borohydride → HCID 23312292, compound

HRID 745820Notes

Reaction equation

HRID 745820 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([CH3:22])[CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[CH:17]=2)[CH2:9][CH2:8]1>O>[OH:3][CH:4]([CH3:22])[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[CH:17]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23312250HCID 23312250, compound

Product 1

HCID 23312292HCID 23312292, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6.0 g of sodium borohydride in 25 ml of water is added dropwise, with stirring and external cooling, to a solution of 6.0 g of 1-(3-oxobutyl)-4-(2-benzofuranyl)-piperidine (cp. Example 8), the manner of addition being such that the reaction temperature does not exceed 30°. The mixture is subsequently stirred for 15 hours at room temperature. The methanol is then evaporated off in vacuo, the aqueous phase remaining being extracted twice with 250 ml of chloroform each time, the chloroform solution dried over sodium sulphate, filtered, and concentrated by evaporation. The residue is dissolved in 500 ml of 2N hydrochloric acid, and the acid solution washed with ether. The aqueous solution is subsequently adjusted by addition of 10% sodium hydroxide solution to have a pH value of 12, 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-hydroxybutyl)-4-(2-benzofuranyl)-piperidine (4-(2-benzofuranyl)-α -methyl-1-piperidinepropanol). The hydrochloride of this is prepared with hydrogen chloride in ethyl acetate, and recrystallised from ethyl acetate, whereupon it melts at 194°-195°.

Workup

  1. customdoes not exceed 30°
  2. stirringThe mixture is subsequently stirred for 15 hours at room temperature
  3. customThe methanol is then evaporated off in vacuo
  4. extractionthe aqueous phase remaining being extracted twice with 250 ml of chloroform each time
  5. dry with materialthe chloroform solution dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. dissolutionThe residue is dissolved in 500 ml of 2N hydrochloric acid
  9. washthe acid solution washed with ether
  10. additionThe aqueous solution is subsequently adjusted by addition of 10% sodium hydroxide solution
  11. extractionextracted with 1 liter of chloroform
  12. dry with materialThe chloroform solution is dried with sodium sulphate
  13. filtrationfiltered
  14. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-fc90203c3b304a41ad382c5bf9a9a5f9
Source dataset
uspto-grants-1986_07
Patent number
US04600719

Reaction notes

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