Water → Swr 00151

HRID 2209967Notes

Reaction equation

HRID 2209967 reaction equation
BrCC[N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]1=[O:14].[NH:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1.[CH2:30](N(CC)CC)[CH3:31].O>CN(C)C=O>[NH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]([CH:18]2[CH2:19][CH2:20][N:15]([CH2:30][CH2:31][C:7]3[C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[NH:4][C:5](=[O:14])[CH:6]=3)[CH2:16][CH2:17]2)=[CH:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 641061662-bromoethyl-2(1H)-quinolinone

Product 1

HCID 3073949Swr 00151Yield 233%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-(2-bromoethyl-2(1H)-quinolinone (II-2) (30 g, 119 mmol) and 3-(4-piperidinyl)-1H-indole (23.8 g, 119 mmol) in dry dimethylformamide 300 ml was added triethylamine (33 ml, 238 mmol) at room temperature and the mixture was allowed to react under the same conditions for 48 hours. Water (600 ml) was poured into the reaction mixture and the mixture was stirred for 15 minutes at room temperature. The separated solid was filtered off by aspiration. The solid was washed with water, dried under reduced pressure and recrystallized with methanol/tetrahydrofuran/water to give the desired product (103 g) (III-2) as white solid (mp 259°-259.5 ° C. (methanol/tetrahydrofuran/water), yield 70.9 %).

Workup

  1. customto react under the same conditions for 48 hours
  2. filtrationThe separated solid was filtered off by aspiration
  3. washThe solid was washed with water
  4. customdried under reduced pressure
  5. customrecrystallized with methanol/tetrahydrofuran/water

Sources & evidence

ORD record
ord-0174b44360ef429a853ef6ebcaf8a732
Source dataset
uspto-grants-1995_10
Patent number
US05457099

Reaction notes

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