Methyl Isocyanate → Ethyl 1-(n-methylaminocarbonyl)-4-oxo-3-piperidinecarboxylate

HRID 432797Notes

Reaction equation

HRID 432797 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5].Cl.C(N(C(C)C)CC)(C)C.[CH3:23][N:24]=[C:25]=[O:26]>ClCCl>[CH3:23][NH:24][C:25]([N:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7]1)=[O:26]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 81531DiisopropylethylamineHCID 1073153-Piperidinecarboxylic acid, 4-oxo-, ethyl ester, hydrochloride (1:1)

Product 1

HCID 18760282Ethyl 1-(n-methylaminocarbonyl)-4-oxo-3-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Commercially available ethyl 4-piperidone-3-carboxylate hydrochloride (203.2 mg; 0.98 mmol) was suspended in dichloromethane (7 ml), diisopropylethylamine (180 μl; 0.99 mmol) was added, followed by commercially available methyl isocyanate and (57 μl; 0.98 mmol). This mixture was stirred at ambient temperature for approximately 3 hours, and then diluted with fresh dichloromethane and washed with water. The dichloromethane solution was dried with anhydrous potassium carbonate and evaporated at ambient temperature under reduced pressure, giving ethyl 1-(N-methylaminocarbonyl)-4-oxo-3-piperidinecarboxylate (74.4 mg) as a white solid. MS m/z (positive ion) 479 (dimer+Na+; 40), 457 (dimer+; 25), 251 (M+Na+; 100), 229 (MH+; 90), 205 (25), 130 (25).

Workup

  1. washwashed with water
  2. dry with materialThe dichloromethane solution was dried with anhydrous potassium carbonate
  3. customevaporated at ambient temperature under reduced pressure

Sources & evidence

ORD record
ord-5c25927d6f514dd4815de0cb4cd844aa
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Reaction notes

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