Potassium Carbonate → 2-Hydroxy-3-(4-phenoxymethylpiperidino)-propoxy-2-ethoxycarbonylindole

HRID 614832Notes

Reaction equation

HRID 614832 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12](O)[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[O:16]1[CH2:33][CH:17]1[CH2:18][N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:21][CH2:20]1.C(=O)([O-])[O-:35].[K+].[K+]>C(#N)C>[OH:35][CH:17]([CH2:18][N:19]1[CH2:20][CH2:21][CH:22]([CH2:25][O:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:23][CH2:24]1)[CH2:33][O:16][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13274763Ethyl 4-hydroxy-1H-indole-2-carboxylateHCID 21327287N-(2,3-epoxypropyl)-4-phenoxymethylpiperidine

Product 1

HCID 867364292-Hydroxy-3-(4-phenoxymethylpiperidino)-propoxy-2-ethoxycarbonylindole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.9 g. 2-ethoxycarbonyl-4-hydroxyindole, 1.7 g. N-(2,3-epoxypropyl)-4-phenoxymethylpiperidine, 1.2 g. potassium carbonate and 50 ml. acetonitrile is heated under reflux for 10 hours. The reaction mixture is then filtered while still hot and the filtrate left to cool overnight. 0.3 g. (15% of theory) 4-[2-hydroxy-3-(4-phenoxymethylpiperidino)-propoxy]-2-ethoxycarbonylindole crystallize out; m.p. 168°-170° C.

Workup

  1. additionA mixture of 0.9 g
  2. temperatureunder reflux for 10 hours
  3. filtrationThe reaction mixture is then filtered while still hot and the filtrate
  4. waitleft
  5. temperatureto cool overnight
  6. custom(15% of theory) 4-[2-hydroxy-3-(4-phenoxymethylpiperidino)-propoxy]-2-ethoxycarbonylindole crystallize out

Sources & evidence

ORD record
ord-4883bb9787fb4ac084753e960ec14d99
Source dataset
uspto-grants-1979_03
Patent number
US04146630

Reaction notes

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