5-Methoxyindole → HCID 22122073, compound

HRID 1858940Notes

Reaction equation

HRID 1858940 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[C:12]1([CH2:18][N:19]2[CH2:24][CH2:23][N:22]([CH:25]3[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]3)[CH2:21][CH2:20]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1CCCC1>C(O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:28]1[CH2:29][CH2:30][CH:25]([N:22]2[CH2:21][CH2:20][N:19]([CH2:18][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:24][CH2:23]2)[CH2:26][CH:27]=1

Participants

6

Reactant 3

HCID 138725-MethoxyindoleHCID 31268PyrrolidineHCID 15338143HCID 15338143, compound

Product 1

HCID 22122073HCID 22122073, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-methoxyindole (3.68 mmole), 4-[4-(phenylmethyl)-1-piperazinyl]cyclohexanone (3.68 mmole), and pyrrolidine (0.25 ml) in ethanol (10 ml) was heated at reflux for 96 hr. The solution was concentrated in vacuo and the residue purified by chromatography on silica eluting with ethyl acetate in hexane to give the product which was converted to the fumarate salt in ethyl acetate (38.4%, mp: 199-200° C.). Calc'd for C26H31N3O.2C2H2O2 : C, 64.45%; H, 6.21%; N, 6.64%. Found: C, 64.42%; H, 6.21%; N, 6.61%.

Workup

  1. temperatureat reflux for 96 hr
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue purified by chromatography on silica eluting with ethyl acetate in hexane
  4. customto give the product which

Sources & evidence

ORD record
ord-5d8789d2874a4ee9b81cdb25b20cc392
Source dataset
uspto-grants-2000_11
Patent number
US06153611

Reaction notes

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