Methylamine → 1-benzyl-N-methylpiperidine-4-carboxamide

HRID 403507Notes

Reaction equation

HRID 403507 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN.[CH2:19]([N:21]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C([O-])(O)=O.[Na+]>C1COCC1.CN(C=O)C>[CH3:19][NH:21][C:14]([CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1)=[O:16]

Participants

8

Reactant 5

HCID 6329MethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 47149831-Benzylpiperidine-4-carboxylic acid

Product 1

HCID 409218631-benzyl-N-methylpiperidine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-benzylpiperidine-4-carboxylic acid (1 g, 4.56 mmol), methylamine (9.12 ml of a 2N solution in THF, 18.2 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.75 g, 9.1 mmol) and 1-hydroxybenzotriazole (0.7 g, 4.56 mmol) in 10 ml DMF was stirred at rt for 3 h. The reaction mixture was poured on saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic layer was washed with NaHCO3 solution and brine, dried (Na2 SO4) and evaporated. Drying in vacuo gave a colorless solid which was used in the next step without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with NaHCO3 solution and brine
  3. customdried (Na2 SO4)
  4. customevaporated
  5. customDrying in vacuo
  6. customgave a colorless solid which
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-46918214ad9f4ede861590323b4039a8
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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