Water → HCID 19379707, compound

HRID 2209968Notes

Reaction equation

HRID 2209968 reaction equation
Br[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:13])[C:5](=[O:14])[CH:4]=1.[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.C(=O)([O-])O.[Na+].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]([CH2:2][C:3]3[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[N:6]([CH3:13])[C:5](=[O:14])[CH:4]=3)[CH2:16][CH2:17]2)=[CH:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 11528942HCID 11528942, compound

Product 1

HCID 19379707HCID 19379707, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-bromomethyl-l-methyl-2(1H)-quinolinone (756 mg, 3 mmol), 3-(4-piperidinyl)-1H-indole (600 mg, 3 mmol) and sodium hydrogencarbonate (378 mg, 4.5 mmol) in dry dimethylformamide (5 ml) was allowed to react at 80 ° C. for 2 hours. The reaction mixture was poured into water and the separated solid was filtered off. The solid was washed with water, dried and then recrystallized from methanol/tetrahydrofuran to give the desired product (III16) (720 mg, yield 65%). Mp 228°-229 ° C. (methanol/tetrahydrofuran).

Workup

  1. customto react at 80 ° C. for 2 hours
  2. filtrationthe separated solid was filtered off
  3. washThe solid was washed with water
  4. customdried
  5. customrecrystallized from methanol/tetrahydrofuran

Sources & evidence

ORD record
ord-dca554ad61c64b6f8f171ad45104fcb7
Source dataset
uspto-grants-1995_10
Patent number
US05457099

Reaction notes

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