1,1'-Carbonyldiimidazole → 4-benzyl-1-(1H-indol-5-yl)piperazine-2,6-dione

HRID 459849

Reaction equation

HRID 459849 reaction equation
[CH2:1]([N:8]([CH2:13][C:14]([OH:16])=O)[CH2:9][C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][CH:34]=[CH:33]2>C1COCC1>[CH2:1]([N:8]1[CH2:9][C:10](=[O:12])[N:29]([C:30]2[CH:31]=[C:32]3[C:36](=[CH:37][CH:38]=2)[NH:35][CH:34]=[CH:33]3)[C:14](=[O:16])[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 77606N-Benzylaminodiacetic acidHCID 788675-Aminoindole

Product 1

HCID 229310254-benzyl-1-(1H-indol-5-yl)piperazine-2,6-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Benzyliminodiacetic acid was reacted with CDI and 5-aminoindole in THF to obtain 4-benzyl-1-(1H-indol-5-yl)piperazine-2,6-dione, which was then reacted with lithium aluminum hydride in THF. Conc. hydrochloric acid and palladium hydroxide were added to an ethanol solution of thus obtained compound and the whole was reacted under a hydrogen atmosphere of 3 atm for 65 hours to obtain an objective compound.

Sources & evidence

ORD record
ord-b6dd4d4e1f0746f5a86b715e167a3784
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Linked notes

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