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

HRID 1351416Notes

Reaction equation

HRID 1351416 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.Cl.[CH3:18][N:19](C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CN>O1CCCC1.ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:19][CH3:18])=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 47149831-Benzylpiperidine-4-carboxylic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-Benzyl 4-piperidinecarboxylic acid (5.00 g, 22.8 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (5.25 g, 27.4 mmol) and 1-hydroxybenzotriazole hydrate (3.84 g, 25.1 mmol) were added to a solution of methylamine (11.4 ml of a 2.0M solution in tetrahydrofuran, 22.8 mmol) in dichloromethane (100 ml). The mixture was stirred for 1 hour at room temperature, then partitioned between dichloromethane and water. The organic layer was separated and washed with brine, dried (MgSO4), filtered and evaporated under reduced pressure to furnish a pale yellow solid, 3.50 g.

Workup

  1. custompartitioned between dichloromethane and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto furnish a pale yellow solid, 3.50 g

Sources & evidence

ORD record
ord-c98c2f2415ae45c6a251024ef89a28d6
Source dataset
uspto-grants-2007_05
Patent number
US07217714B1

Reaction notes

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