Methanol → 4-{3-{4-(4-Ethylphenyl)methylamino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate hydrochloride

HRID 1066179Notes

Reaction equation

HRID 1066179 reaction equation
[ClH:1].[CH2:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]2[CH:36]=[CH:35][C:15]([C:16]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH2:27][CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[CH:19]=3)=[O:17])=[CH:14][C:13]=2[O:37][CH2:38][CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][N:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[O:53][CH3:54])[CH2:43][CH2:42]2)=[CH:6][CH:5]=1)[CH3:3].CO.[OH-].[K+]>O1CCCC1>[ClH:1].[CH2:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]2[CH:36]=[CH:35][C:15]([C:16]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:19]=3)=[O:17])=[CH:14][C:13]=2[O:37][CH2:38][CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][N:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[O:53][CH3:54])[CH2:43][CH2:42]2)=[CH:6][CH:5]=1)[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 21197984Ethyl 4-{3-{4-(4-ethylphenyl)methylamino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy)benzoyl}indol-1-yl}butanoate hydrochloride

Product 1

HCID 702316134-{3-{4-(4-Ethylphenyl)methylamino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate hydrochlorideYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-{3-{4-(4-ethylphenyl)methylamino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate hydrochloride (40.8 g) was dissolved in tetrahydrofuran (200 ml), and methanol (200 ml) and potassium hydroxide (11.3 g) were added to the solution. The resultant mixture was refluxed for one hour and 30 minutes. The reaction mixture was cooled and concentrated under reduced pressure. Water (1.2 l) was added to dilute the residue, and the resultant solution was poured into 1N hydrochloric acid (400 ml), to thereby precipitate crystals. The crystals were collected by filtration. The collected crystals were washed with water, dried, and recrystallized from 95% ethanol, to thereby obtain 33.8 g of 4-{3-{4-(4-ethylphenyl)methylamino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate hydrochloride as pale yellow crystals.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionWater (1.2 l) was added
  4. additionto dilute the residue
  5. additionthe resultant solution was poured into 1N hydrochloric acid (400 ml)
  6. customto thereby precipitate crystals
  7. filtrationThe crystals were collected by filtration
  8. washThe collected crystals were washed with water
  9. customdried
  10. customrecrystallized from 95% ethanol

Sources & evidence

ORD record
ord-8234147a1b074cfca81bc1a68a092201
Source dataset
uspto-grants-2001_06
Patent number
US06242449B1

Reaction notes

Loading…