Methylamine → tert-Butyl 4-(methylamino)piperidine-1-carboxylate

HRID 2353135Notes

Reaction equation

HRID 2353135 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN.[C:17]([BH3-])#[N:18].[Na+]>CO.C(Cl)Cl>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:18][CH3:17])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylateYield 79.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Amine preparation: To a solution of 1-BOC-4-piperidone (1.0 g) in MeOH (10 mL) was added a solution of freshly prepared methylamine in MeOH (1.0 mL). The reaction mixture was stirred for 1 h and then sodium cyanoborohydride (0.315 g) was added. After stirring for 24 h the reaction mixture was then diluted with DCM, washed with sodium bicarbonate solution, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography to yield 4-methylamino-piperidine-1-carboxylic acid tert-butyl ester (0.85 g).

Workup

  1. stirringAfter stirring for 24 h the reaction mixture
  2. washwashed with sodium bicarbonate solution
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-376b54acceb44585b2997e9b50831f02
Source dataset
uspto-grants-2010_07
Patent number
US07750002B2

Reaction notes

Loading…