Hydrochloric Acid → Ethyl 4-{3-{4-(4-ethylphenyl)methylamino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy)benzoyl}indol-1-yl}butanoate hydrochloride

HRID 1066178Notes

Reaction equation

HRID 1066178 reaction equation
[Cl:1]CCCO[C:6]1[CH:30]=[C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([CH2:39][CH3:40])=[CH:35][CH:34]=2)[CH:28]=[CH:27][C:7]=1[C:8]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:11]=1)=[O:9].Cl.[CH3:42][O:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1.[I-].[K+].Cl>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[ClH:1].[CH2:39]([C:36]1[CH:37]=[CH:38][C:33]([CH2:32][NH:31][C:29]2[CH:30]=[CH:6][C:7]([C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:11]=3)=[O:9])=[CH:27][C:28]=2[O:9][CH2:8][CH2:7][CH2:6][N:53]2[CH2:54][CH2:55][N:50]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=3[O:43][CH3:42])[CH2:51][CH2:52]2)=[CH:34][CH:35]=1)[CH3:40]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochlorideHCID 21197980Ethyl 4-{3-[3-chloropropoxy-4-(4-ethylphenyl)methylaminobenzoyl]indol-1-yl}butanoate

Product 1

HCID 21197984Ethyl 4-{3-{4-(4-ethylphenyl)methylamino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy)benzoyl}indol-1-yl}butanoate hydrochlorideYield 142.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 4-{3-[3-chloropropoxy-4-(4-ethylphenyl)methylaminobenzoyl]indol-1-yl}butanoate (44.5 g) was dissolved in N,N-dimethylformamide (230 ml), and 1-(2-methoxyphenyl)piperazine hydrochloride (36.2 g), potassium iodide (52.5 g), and triethylamine (46 ml) were added to the solution. The resultant mixture was stirred at 90° C. for one hour. The reaction mixture was cooled and poured into ethyl acetate (230 ml) and 1N hydrochloric acid (460 ml) was added. Crystals so precipitated were collected by filtration and recrystallized from 90% ethanol, to thereby obtain 42.6 g of ethyl 4-{3-{4-(4-ethylphenyl)methylamino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy)benzoyl}indol-1-yl}butanoate hydrochloride as colorless crystals.

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionwas added
  3. customCrystals so precipitated
  4. filtrationwere collected by filtration
  5. customrecrystallized from 90% ethanol

Sources & evidence

ORD record
ord-cea1863352ff43f59f2d54dbee054e4f
Source dataset
uspto-grants-2001_06
Patent number
US06242449B1

Reaction notes

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