Methylamine → 1-benzyl-N-methyl-5-oxopyrrolidine-3-carboxamide

HRID 247849Notes

Reaction equation

HRID 247849 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13](O)=[O:14])[CH2:10][C:9]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](N1C=CN=C1)([N:19]1C=CN=C1)=O.CN>C(Cl)Cl>[CH3:17][NH:19][C:13]([CH:11]1[CH2:12][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9](=[O:16])[CH2:10]1)=[O:14]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 990241-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid

Product 1

HCID 134917941-benzyl-N-methyl-5-oxopyrrolidine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.2 mole of (1-benzyl-2-oxo-4-pyrrolidinyl)carboxylic acid (described in Journal of Organic Chemistry, 1961; 26: p 1519) is dissolved in 200 cm3 of methylene chloride. The mixture is treated with 32.4 g of carbonyldiimidazole. It is left in contact for 1 hour and then a solution consisting of 20 g of methylamine and 200 cm3 of methylene chloride is added. The mixture is left in contact for 12 hours at room temperature, washed with water and then dried over magnesium sulfate. An oil which is the expected compound is obtained.

Workup

  1. additionis added
  2. waitThe mixture is left in contact for 12 hours at room temperature
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customis obtained

Sources & evidence

ORD record
ord-3ae94fa6f8c74b52a1ff9442c1155c83
Source dataset
uspto-grants-1993_05
Patent number
US05208243

Reaction notes

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