Methanol → [1-(Pyridin-4-yl)piperidin-4-yl]methanamine

HRID 1193328Notes

Reaction equation

HRID 1193328 reaction equation
B(F)(F)F.CCOCC.[N:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]#[N:23])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1.CO>C1COCC1>[N:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:17][CH2:18][CH:19]([CH2:22][NH2:23])[CH2:20][CH2:21]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8000Boron trifluoride etherateHCID 66798807HCID 66798807, compound

Product 1

HCID 10607746[1-(Pyridin-4-yl)piperidin-4-yl]methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., BH3-DMS (1.089 ml, 11.336 mmol, 4 eq) and BF3-Et2O (355 4 2.83 mmol, 1 eq) were added to a solution of 1-(pyridin-4-yl)piperidine-4-carbonitrile (530 mg, 2.83 mmol, 1 eq) in THF (10 ml) and heated for 1 h at boiling temperature. The reaction mixture was hydrolyzed with MeOH (15 ml) and concentrated under reduced pressure. The white solid so obtained was used in the next stage without being purified further. Yield: quantitative

Workup

  1. temperatureheated for 1 h
  2. concentrationconcentrated under reduced pressure
  3. customThe white solid so obtained
  4. customwithout being purified further

Sources & evidence

ORD record
ord-6a214f77cfdc4d3298f3b70c5cb518eb
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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