Dimethylamine → N,N-Dimethyl-3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionamide

HRID 1836120Notes

Reaction equation

HRID 1836120 reaction equation
[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:6][CH:5]=[C:4]([CH2:11][CH2:12][C:13]([OH:15])=O)[C:3]1=2.[C:16](N1C=CN=C1)([N:18]1C=CN=[CH:19]1)=O.CNC>ClCCl.O1CCCC1>[CH3:16][N:18]([CH3:19])[C:13](=[O:15])[CH2:12][CH2:11][C:4]1[C:3]2[C:2](=[O:1])[CH2:10][CH2:9][CH2:8][C:7]=2[NH:6][CH:5]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 158327213-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoic acid

Product 1

HCID 22571143N,N-Dimethyl-3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionamideYield 60%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3-(4-Oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (12 g, 0.06 mol) was suspended in 80 ml of dichloromethane and carbonyldiimidazole (11.3 g, 0.07 mol) was added with stirring. After 30 minutes 58 ml of 2.0 M dimethylamine in tetrahydrofuran was added. After one hour the solvent was rotary evaporated. The residue was redissolved in dichloromethane, washed with 1 N hydrochloric acid and brine, dried over anhydrous magnesium sulfate and rotary evaporated. The solid residue was washed with ethyl acetate and dried under vacuum to give N, N-dimethyl-3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionamide (8 g, 60% yield).

Workup

  1. washwashed with 1 N hydrochloric acid and brine
  2. dry with materialdried over anhydrous magnesium sulfate and rotary evaporated
  3. washThe solid residue was washed with ethyl acetate
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b4dc9bce73a04110a5d4b90d1d1e958a
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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