Sodium borohydride → 4-Piperazinyl-2,6-bis-hydroxymethyl pyridine

HRID 411873Notes

Reaction equation

HRID 411873 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:9]=[C:8]([C:18](OCC)=[O:19])[N:7]=1)=O)C.[BH4-].[Na+].[Cl-].[Cl-].[Ca+2]>C1COCC1.[Cl-].[Na+].O>[N:12]1([C:10]2[CH:11]=[C:6]([CH2:4][OH:3])[N:7]=[C:8]([CH2:18][OH:19])[CH:9]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 85702736Diethyl-4-piperazinyl-2,6-pyridinedicarboxylate

Product 1

HCID 212573294-Piperazinyl-2,6-bis-hydroxymethyl pyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Diethyl-4-piperazinyl-2,6-pyridinedicarboxylate is dissolved in THF and treated with NaBH4 and CaCl2. Brine is added and the organic phase is separated. The organic phase is washed with brine, dried (Na2SO4) and the solvent is evaporated. The residue is purified by flash chromatography on a silica gel column to give the title compound.

Workup

  1. customthe organic phase is separated
  2. washThe organic phase is washed with brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent is evaporated
  5. customThe residue is purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-602c02c2f14a4ed7a246a7f6ec650972
Source dataset
uspto-grants-2003_05
Patent number
US06559303B1

Reaction notes

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