Diethylamine → 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethylpropionamide

HRID 1372396Notes

Reaction equation

HRID 1372396 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH2:12][C:13]([OH:15])=O)[C:5]=2[C:4](=[O:16])[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:30]([NH:32][CH2:33][CH3:34])[CH3:31]>ClCCl>[CH3:17][C:2]1([CH3:1])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH2:12][C:13]([N:32]([CH2:33][CH3:34])[CH2:30][CH3:31])=[O:15])[C:5]=2[C:4](=[O:16])[CH2:3]1

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 210718994,5,6,7-H4-6,6-Me2-4-oxo-indole-3-propanoic acid

Product 1

HCID 225710523-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethylpropionamideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1.18 g of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (5 mmol) in dichloromethane (25 mL) was added 0.97 g (6 mmol) of carbonyldiimidazole. After stirring at room temperature for 2 hours, 2.1 mL (20 mmol) of diethylamine was added. The mixture was stirred at room temperature overnight. The reaction was concentrated and the residue dissolved in dichloromethane, washed with brine, dried and concentrated to give 1.2 g (83% yield) of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethyl-propionamide as a white solid. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 10.91 (br s, 1H, NH), 6.46 (s, 1H), 3.20–3.29 (m, 4H, 2×CH2), 2.72–2.76 (m, 2H, CH2), 2.57 (s, 2H, CH2), 2.45 (m, 2H, CH2), 2.17 (s, 2H, CH2), 0.96–1.06 (m, 12H, 4×CH3). MS m/z 290 [M+].

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. concentrationThe reaction was concentrated
  3. dissolutionthe residue dissolved in dichloromethane
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-793e3c418f9a4706bd9ef5e0e390f21c
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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