Triethylamine → HCID 54025773, compound

HRID 1683918Notes

Reaction equation

HRID 1683918 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17].Cl[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][C:20]=1[N+:27]([O-:29])=[O:28].C(N(CC)CC)C>C(O)C>[C:23]([C:22]1[CH:25]=[CH:26][C:19]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3[CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH3:17])=[C:20]([N+:27]([O-:29])=[O:28])[CH:21]=1)#[N:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 10376533(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Product 1

HCID 54025773HCID 54025773, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole end 4-chloro-3-nitrobenzonitrile were used. Triethylamine was used as base, absolute ethanol was used as solvent, and the reaction was heated at reflux for 4 hours. Column chromatography afforded the title compound (80%) as a red solid: mp, 170°-171.0° C.; 13C NMR (CDCl3) δ147.3, 137.1, 135.4, 132.0, 131.4, 128.6, 128.0, 125.3, 120.6, 117.9, 117.1, 116.3, 113.1, 111.9, 99.1, 68.1, 57.3, 40.6, 31.2, 28.1, 21.9, Anal. calcd for C21H21N5O2.0.05 CH2Cl2 : C, 66.59; H, 5.60; N, 18.44. Found: C, 66.56; H, 5.26; N, 18.42.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 4 hours

Sources & evidence

ORD record
ord-1c2436132c924e509fe64300dc8edd2e
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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