Sodium borohydride → (1-Methyl-4-piperidinyl)[3-(2-phenylethyl)-2-pyridinyl]methanol

HRID 1534590Notes

Reaction equation

HRID 1534590 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]([C:10]2[C:15]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:9])[CH2:4][CH2:3]1.[BH4-].[Na+]>CO.O>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH:8]([C:10]2[C:15]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=[CH:12][N:11]=2)[OH:9])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 14885588(1-Methylpiperidin-4-yl)[3-(2-phenylethyl)pyridin-2-yl]methanone

Product 1

HCID 19918405(1-Methyl-4-piperidinyl)[3-(2-phenylethyl)-2-pyridinyl]methanolYield 87.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 5.0g (16.2 mmole) of (1-methyl-4-piperidinyl)[3-(2-phenylethyl)-2-pyridinyl]methanone (which can be prepared in the same manner as described in Preparative Example 1, Steps A-D) in 70 mL of methanol was added portionwise 0.8 g (21.1 mmole) of sodium borohydride. The next day the solution was concentrated in vacuo to give a slurry which was dissolved in water and extracted with CHCl3. The combined organic portions were dried over MgSO4, filtered, and concentrated in vacuo to provide a liquid which was distilled (bp 190°-195° C. 1 mm Hg) to give 4.4 gms of the title compound as a viscous oil.

Workup

  1. customcan be prepared in the same manner
  2. concentrationThe next day the solution was concentrated in vacuo
  3. customto give a slurry which
  4. extractionextracted with CHCl3
  5. dry with materialThe combined organic portions were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide a liquid which
  9. distillationwas distilled (bp 190°-195° C. 1 mm Hg)

Sources & evidence

ORD record
ord-69f3cc63764c42e49440483911fdb1da
Source dataset
uspto-grants-1992_02
Patent number
US05089496

Reaction notes

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