Acetic Acid → N-methyl-1-(pyridin-4-yl)piperidin-4-amine

HRID 1193306Notes

Reaction equation

HRID 1193306 reaction equation
C(O)(=O)C.[N:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.Cl.CN.[BH3-][C:22]#[N:23].[Na+]>CO>[CH3:22][NH:23][CH:14]1[CH2:15][CH2:16][N:11]([C:8]2[CH:9]=[CH:10][N:5]=[CH:6][CH:7]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 113327931-(Pyridin-4-yl)piperidin-4-one

Product 1

HCID 17852018N-methyl-1-(pyridin-4-yl)piperidin-4-amineYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid (150 μl) was added to a solution of 1-(pyridin-4-yl)piperidin-4-one (450 mg, 2.55 mmol, 1 eq) and methylamine hydrochloride (190 mg, 2.81 mmol, 1.1 eq) in methanol (10 ml), and stirring was carried out for 20 min at RT. Then NaBH3CN (166 mg, 2.81 mmol, 1.1 eq) was added in portions and stirring was carried out for 16 h at RT. The solvent was concentrated, and the residue was taken up in chloroform (100 ml), washed with sat. K2CO3 solution (30 ml) and sat. NaCl solution (30 ml), dried over sodium sulfate and concentrated under reduced pressure. The product (yellow solid) was used in the next stage without being purified further. Yield: 82% (400 mg, 2.09 mmol).

Workup

  1. stirringstirring
  2. waitwas carried out for 16 h at RT
  3. concentrationThe solvent was concentrated
  4. washwashed with sat. K2CO3 solution (30 ml) and sat. NaCl solution (30 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customwithout being purified further

Sources & evidence

ORD record
ord-4c15733dee7b450f9c264e8ab8b04d2c
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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