Ethanol → HCID 15391294, compound

HRID 1080699Notes

Reaction equation

HRID 1080699 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][CH:10]2[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.[CH3:22][CH2:23][OH:24]>>[C:23]([C:13]1[CH:12]=[C:11]2[C:10](=[CH:15][CH:14]=1)[NH:9][CH:8]=[C:7]2[C:1]1[CH2:6][CH2:5][CH:4]([NH:17][CH2:21][CH2:20][C:19]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:18]=2)[CH2:3][CH:2]=1)(=[O:24])[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 31268PyrrolidineHCID 15290849HCID 15290849, compound

Product 1

HCID 15391294HCID 15391294, compoundYield 96%

Procedure

5-Acetyl-l-H-indole1 (3.18 g, 0.02 mol), 4-[(2-phenylethyl)amino]cyclohexanone (5.2 g, 0.024 mol) and pyrrolidine (5 mL) were dissolved in EtOH (30 mL) and refluxed for 48 h. The solvent was removed in vacuo. Silica gel chromatography (20-100% EtOAc gradient in hexane followed by 5-20% MeOH gradient in EtOAc) of the residue yielded the product (6.93 g, 96%). Treatment of this material with fumaric acid in MeOH afforded the fumarate salt which was recrystallized from MeOH/EtOAc (2.6 g, 30.5%): mp 266°-269° C. Anal. Calcd for C24H26N2).0.7 C4H4O4 : C 73.25; H 6.84; N 6.37. Found: C 73.20; H 6.60; N 6.37.

Workup

  1. temperaturerefluxed for 48 h
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5c913d889903431d8df090eaa9e95d03
Source dataset
uspto-grants-1996_12
Patent number
US05583149

Reaction notes

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