Acetic Acid → HCID 43166646, compound

HRID 1193402Notes

Reaction equation

HRID 1193402 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.CC(O)=O.[CH:18]([NH2:21])([CH3:20])[CH3:19].[BH3-]C#N.[Na+]>CO>[CH:18]([NH:21][CH:10]1[CH2:11][CH2:12][N:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:8][CH2:9]1)([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6363IsopropylamineHCID 5003444Sodium cyanoborohydrideHCID 113327931-(Pyridin-4-yl)piperidin-4-one

Product 1

HCID 43166646HCID 43166646, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(Pyridin-4-yl)piperidin-4-one (1.5 g, 8.52 mmol, 1.0 eq.) was dissolved in MeOH (40 ml); AcOH (0.6 ml) and isopropylamine (1.39 ml, 17.04 mmol, 2.0 eq.) were added and the mixture was stirred for 3 hours at RT. NaCNBH3 (856 mg, 12.78 mmol, 1.5 eq.) was then added in portions at 0° C. and stirring was carried out for a further 14 hours at RT. The reaction mixture was concentrated under reduced pressure and the residue was taken up in water (100 ml) and extracted with DCM (150 ml). The org. phase was washed with sat. NaHCO3 solution (100 ml), dried over sodium sulfate, concentrated and purified by column chromatography (Alox, 2% MeOH in DCM). Yield: 64% (1.2 g, 5.47 mmol)

Workup

  1. stirringstirring
  2. waitwas carried out for a further 14 hours at RT
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionextracted with DCM (150 ml)
  5. washphase was washed with sat. NaHCO3 solution (100 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. custompurified by column chromatography (Alox, 2% MeOH in DCM)

Sources & evidence

ORD record
ord-f6de22e243064a67b9ec1ffb4c6dae76
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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