N-Carbethoxyphthalimide → HCID 22611405, compound

HRID 726002Notes

Reaction equation

HRID 726002 reaction equation
[NH2:1]C1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1.[C:18]([N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33])(OCC)=[O:19]>ClCCl>[OH-:19].[NH4+:1].[C:24]1(=[O:33])[N:23]([C:18]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3[CH:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]12

Participants

5

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 118312203-(1-Methylpiperidin-4-yl)-1h-indol-5-amine

Product 2

HCID 14923Ammonium HydroxideHCID 22611405HCID 22611405, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.458 gm (2.0 mMol) 5-amino-3-(1-methylpiperidin-4-yl)-1H-indole in 8.0 mL dichloromethane were added 0.438 gm (2.0 mMol) N-carbethoxyphthalimide. The reaction mixture was stirred 18 hours at ambient temperature, at which time the solvent was removed under reduced pressure. The residue was subjected to flash chromatography, eluting with 100:20:0.5 dichloromethane:methanol:ammonium hydroxide, giving 0.467 gm (65%) of 5-phthalimido-3-(1-methylpiperidin-4-yl)-1H-indole as a yellow foam. The yellow foam was dissolved in a mixture of methanol:ethyl acetate and to it was added an equivalent of oxalic acid. The colorless precipitate which formed was recrystallized from methanol to give 0.267 gm of the title compound as colorless crystals.

Workup

  1. customwas removed under reduced pressure
  2. washeluting with 100:20:0.5 dichloromethane

Sources & evidence

ORD record
ord-91ee40fe432746d5b912cadef88ffd96
Source dataset
uspto-grants-1998_01
Patent number
US05708008

Reaction notes

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