Water → 6-acetylamino-4-[2-[4-(1H-indol-3-Yl)-1-piperidinyl]ethyl]-2(1H)-quinolinone

HRID 2209976Notes

Reaction equation

HRID 2209976 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[CH2:13][CH2:14][N: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.C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38].O>CN(C)C=O>[C:37]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:19][CH2:20]1)(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 193796936-amino-4-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-2(1H)-quinolinone

Product 1

HCID 193796736-acetylamino-4-[2-[4-(1H-indol-3-Yl)-1-piperidinyl]ethyl]-2(1H)-quinolinoneYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-amino-4-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-2(1H)-quinolinone (III-20) (1 g, 2.59 mmol) in dimethylformamide (8 ml) was added triethylamine (0.7 ml, 5 mmol). To the mixture was added dropwise acetyl chloride (0.2 ml, 2.75 mmol) at 0 ° C. and the mixture was stirred at the same temperature for 15 minutes. The reaction mixture was poured into water and the separated solid was filtered off. After washing with water and drying, the solid was recrystallized from a mixture of methanol, tetrahydrofuran and water to give the desired product (III-21) (900 mg) as pale yellow crystals (yield 81.1%, mp 180°-183° C. (methanol/tetrahydrofuran/water).

Workup

  1. filtrationthe separated solid was filtered off
  2. washAfter washing with water
  3. customdrying
  4. customthe solid was recrystallized from a mixture of methanol, tetrahydrofuran and water

Sources & evidence

ORD record
ord-4b95683d4e324d3585bae57c5eed4d83
Source dataset
uspto-grants-1995_10
Patent number
US05457099

Reaction notes

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