Sodium borohydride → HCID 59589479, compound

HRID 630245Notes

Reaction equation

HRID 630245 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[N:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59589361HCID 59589361, compound

Product 1

HCID 59589479HCID 59589479, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-(4-ethylpiperazin-1-yl)pyridine-3-carbaldehyde (6.9 g, 31.46 mmol) in anhydrous ethanol (80 mL) was added at 0° C. sodium borohydride (2.38 g, 62.93 mmol). The reaction mixture was stirred at room temperature for 1 hour and then quenched with water. The solvent was evaporated, and the mixture was extracted with ethyl acetate (2×200 mL). The organic layer was separated, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated to provide [6-(4-ethylpiperazin-1-yl)pyridin-3-yl]methanol as a syrup (6.61 g, 95% yield); 1H NMR (400 MHz, DMSO-d6): δ 0.99 (t, 3H), 2.31 (q, 2H), 2.39 (m, 4H), 3.42 (m, 4H), 4.32 (s, 2H), 4.98 (s, 1H), 6.78 (d, J=8.6 Hz, 1H), 7.82 (d, J=8.6 Hz, 1H), 8.01 (s, 1H); LRMS (ES+) m/z 221.3.

Workup

  1. customquenched with water
  2. customThe solvent was evaporated
  3. extractionthe mixture was extracted with ethyl acetate (2×200 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-fdf3fbd437324dc79a59478f9113ac58
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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