Water → HCID 20098367, compound

HRID 1091144Notes

Reaction equation

HRID 1091144 reaction equation
CC(N[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:28]=[CH:27][CH:26]=[CH:25][C:12]=1[C:13]([NH:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH:18]=[CH:19][NH:20]2)=[O:14])(C)C.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH2:41][CH2:42][N:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)[CH:34]=[C:35]([O:39][CH3:40])[C:36]=1[O:37][CH3:38].C(=O)([O-])[O-].[Na+].[Na+].O>C(O)C>[NH:20]1[C:21]2[C:17](=[C:16]([NH:15][C:13](=[O:14])[C:12]3[CH:25]=[CH:26][CH:27]=[CH:28][C:11]=3[O:10][CH2:9][CH2:8][CH2:7][CH2:6][N:46]3[CH2:47][CH2:48][N:43]([CH2:42][CH2:41][C:33]4[CH:32]=[C:31]([O:30][CH3:29])[C:36]([O:37][CH3:38])=[C:35]([O:39][CH3:40])[CH:34]=4)[CH2:44][CH2:45]3)[CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 3075941HCID 3075941, compoundHCID 13772352HCID 13772352, compound

Product 1

HCID 20098367HCID 20098367, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.5 g of 2-(4-bromobutyoxy)-N-(1H-indol-4-yl)benzamide of Example 33, 2.71 g of 1-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazine [German Patent No. 3,347,173] and 0.683 g of sodium carbonate in 25 ml of ethanol were heated to 60° C. for 10 hours and the mixture is cooled and poured into water and extracted with ethyl acetate. The extract was washed with water and dried and the solvents were evaporated under reduced pressure. The residue was chromatographed over silica (eluant: chloroform/acetone/triethylamine 6:3:1) to obtain 3.51 g of N-(1H-indol-4-yl)-2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]-1-piperazinyl]butoxy]benzamide.

Workup

  1. temperaturethe mixture is cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. customthe solvents were evaporated under reduced pressure
  6. customThe residue was chromatographed over silica (eluant: chloroform/acetone/triethylamine 6:3:1)

Sources & evidence

ORD record
ord-2113b3518cf945c2a7179e41ac366a95
Source dataset
uspto-grants-1992_01
Patent number
US05084455

Reaction notes

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