Methylamine → 1-Methyl-4-(methylamino)piperidine

HRID 861083Notes

Reaction equation

HRID 861083 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.O1CCCC1.[CH3:14][NH2:15]>CO.[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:15][CH3:14])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 740491-Methyl-4-piperidone

Product 1

HCID 5663231-Methyl-4-(methylamino)piperidineYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-methyl-4-piperidone (20 g, 0.18 mol) in methanol:tetrahydrofuran (100 mL, 1:1) and methyl amine (2 M in tetrahydrofuran, 3 mole excess) was placed in a Parr shaker with 5% Pd/C and hydrogenated for two hours at 60 psi and 70° C. The catalyst was filtered and the filtrate concentrated on the rotary evaporator. The crude material was distilled at 44–45° C. at 0.3 mm Hg to give 20 g (87%) of 1-methyl-4-methylaminopiperidine. Anal. Calc'd for C7H16N2: C, 65.57; H, 12.58; N, 21.85. Found: C, 65.49; H, 12.44; N: 21,49.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate concentrated on the rotary evaporator
  3. distillationThe crude material was distilled at 44–45° C. at 0.3 mm Hg

Sources & evidence

ORD record
ord-977f3b663948465fba5d18e8b0f60bfd
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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