Carbon Dioxide → 1-(7-Methoxy-1-naphthyl)-4-benzyl-2,6-piperazinedione

HRID 373100

Reaction equation

HRID 373100 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([N:20]([CH2:25][C:26]([OH:28])=O)[CH2:21][C:22]([OH:24])=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)=O.[NH2:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([O:43][CH3:44])[CH:41]=2)[CH:36]=[CH:35][CH:34]=1>O1CCCC1.C(O)C>[CH3:44][O:43][C:40]1[CH:41]=[C:42]2[C:37]([CH:36]=[CH:35][CH:34]=[C:33]2[N:32]2[C:22](=[O:24])[CH2:21][N:20]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:25][C:26]2=[O:28])=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 682631,1'-CarbonyldiimidazoleHCID 77606N-Benzylaminodiacetic acidHCID 2358177-Methoxynaphthalen-1-amine

Product 1

HCID 198084871-(7-Methoxy-1-naphthyl)-4-benzyl-2,6-piperazinedioneYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

126 mmol (2.2 equivalents) of carbonyldiimidazole are added to a suspension containing 58 mmol (1 equivalent) of N-benzyliminodiacetic acid in 200 ml of anhydrous tetrahydrofuran. The mixture is brought to reflux until the evolution of CO2 has ceased. A solution containing 58 mmol (1 equivalent) of 1-amino-7-methoxynaphthalene in 40 ml of anhydrous tetrahydrofuran is then added to the above mixture. The resulting mixture is brought to reflux for 20 hours, the solvent is evaporated off and the residue obtained is taken up with 300 ml of anhydrous ethanol. The precipitate formed is filtered off and then dissolved in 200 ml of dichloromethane. The insoluble matter is filtered off and the filtrate concentrated. The expected product is then obtained after taking up in isopropyl ether followed by filtration.

Workup

  1. additionis then added to the above mixture
  2. temperatureto reflux for 20 hours
  3. customthe solvent is evaporated off
  4. customthe residue obtained
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. dissolutiondissolved in 200 ml of dichloromethane
  8. filtrationThe insoluble matter is filtered off
  9. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-0772976ce0b64442a6231cf527145f77
Source dataset
uspto-grants-1992_11
Patent number
US05162324

Linked notes

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