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

HRID 1372392Notes

Reaction equation

HRID 1372392 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](O)=[O:14])[C:5]=2[C:4](=[O:16])[CH2:3]1.[C:18](N1C=CN=C1)([N:20]1C=CN=[CH:21]1)=O.CNC>ClCCl.O1CCCC1>[CH3:1][C:2]1([CH3:17])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH2:12][C:13]([N:20]([CH3:21])[CH3:18])=[O:14])[C:5]=2[C:4](=[O:16])[CH2:3]1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 210718994,5,6,7-H4-6,6-Me2-4-oxo-indole-3-propanoic acid

Product 1

HCID 225711373-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-dimethyl-propionamideYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (1.65 g, 7 mmol) in dichloromethane (15 mL) was added 1.36 g (8.4 mmol) of carbonyldiimidazole. The mixture was stirred at room temperature until the solution became clear. To the mixture was added dimethylamine (14 mL of a 2.0M solution in tetrahydrofuran). The mixture was stirred at room temperature overnight and then concentrated. The residue was redissloved in dichloromethane, washed with brine and concentrated. The solid was washed with ethyl acetate until it became white and dried to give 1.4 g (78% yield) of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-dimethyl-propionamide. 1H-NMR (360 MHz, diemthylsulfoxide-d6) δ10.93 (br s, 1H, NH), 6.48 (s, 1H), 2.94 (s, 3H, CH3), 2.79 (s, 3H, CH3), 2.72 (m, 2H, CH2), 2.57 (s, 2H, CH2), 2.48 (m, 2H, CH2), 2.17 (s, 2H, CH2), 1.00 (m, 6H, 2×CH3). MS m/z 262 [M+].

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. concentrationconcentrated
  3. washwashed with brine
  4. concentrationconcentrated
  5. washThe solid was washed with ethyl acetate until it
  6. customdried

Sources & evidence

ORD record
ord-9b98c204ede44052a2fee3f84418ea88
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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