Water → Ethyl 4-{3-{4-(4-methylphenylmethoxy)-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate

HRID 962766

Reaction equation

HRID 962766 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:26]=[CH:25][C:13]([C:14]([C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)=[O:15])=[CH:12][C:11]=2[O:27][CH2:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][N:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH3:44])[CH2:33][CH2:32]2)=[CH:4][CH:3]=1.BrCC[CH2:48][CH2:49][CH2:50][C:51]([O-])=[O:52].[C:54](=O)([O-])[O-].[K+].[K+].O.CN(C)[CH:63]=[O:64]>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:26]=[CH:25][C:13]([C:14]([C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]([CH2:48][CH2:49][CH2:50][C:51]([O:64][CH2:63][CH3:54])=[O:52])[CH:17]=3)=[O:15])=[CH:12][C:11]=2[O:27][CH2:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][N:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH3:44])[CH2:33][CH2:32]2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 69998686-BromohexanoateHCID 22435861HCID 22435861, compound

Product 1

HCID 19085533Ethyl 4-{3-{4-(4-methylphenylmethoxy)-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate

Conditions

Temperature
60 °C

Procedure

3-{4-(4-Methylphenylmethoxy)-3-{3-[4-(2-methoxyphenyl) piperazin-1-yl]propoxy}benzoyl}indole (0.12 g) obtained in Step 4 was dissolved in N,N-dimethylformamide (2 ml). 4-Bromoethylbutyrate (52 mg) and potassium carbonate (33 mg) were added to the resultant solution and stirred for 3 hours at 60° C. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The resultant extract was washed with brine and then dried. The solvent was distilled off. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1), obtaining 0.11 g of ethyl 4-{3-{4-(4-methylphenylmethoxy)-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}-indol-1-yl}butanoate as a light brown oily substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. extractionThe resultant extract
  3. washwas washed with brine
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-5e926813a29041e49f6c8bc30f5304e4
Source dataset
uspto-grants-1998_06
Patent number
US05760040

Linked notes

Loading…