Dimethylamine → 3-(2,4-dimethyl-1H-pyrrol-3-yl)-N,N-dimethyl-propionamide

HRID 2120240Notes

Reaction equation

HRID 2120240 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:12])[C:6]=1[CH2:7][CH2:8][C:9](O)=[O:10].[C:13](N1C=CN=C1)([N:15]1C=CN=[CH:16]1)=O.CNC.C(N(CC)C(C)C)(C)C>ClCCl.O1CCCC1>[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:12])[C:6]=1[CH2:7][CH2:8][C:9]([N:15]([CH3:16])[CH3:13])=[O:10]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 15125193-(2,4-dimethyl-1H-pyrrol-3-yl)propanoic Acid

Product 1

HCID 234390693-(2,4-dimethyl-1H-pyrrol-3-yl)-N,N-dimethyl-propionamideYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the suspension of 3-(2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid (10 g, 60.8 mmol) in 60 mL of dichloromethane was added 1,1′-carbonyldiimidazole (11.6 g, 71.8 mmol) followed by the addition of 2 M dimethylamine solution in tetrahydrofuran (30 mL) and N,N-diisopropylethylamine (Hunig's base, 10 mL, 60.8 mmol). The dark red reaction mixture was stirred at room temperature overnight and poured into ice water. The organic layer was washed with brine until pH of 6, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified on a silica gel column eluting with dichloromethane-methanol (98:2) to give 9.8 g (83%) of 3-(2,4-dimethyl-1H-pyrrol-3-yl)-N,N-dimethyl-propionamide as a yellow oil.

Workup

  1. customThe dark red reaction mixture
  2. washThe organic layer was washed with brine until pH of 6
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified on a silica gel column
  6. washeluting with dichloromethane-methanol (98:2)

Sources & evidence

ORD record
ord-d2fd590407ca4b07b03c8784468b44fb
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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