Benzylamine → HCID 22903655, compound

HRID 1489157Notes

Reaction equation

HRID 1489157 reaction equation
ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:26]([N:33]1[C:37](=[O:38])[CH2:36][C:35]([C:44]([O-:46])=O)([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH2:47]([NH2:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>O1CCCC1>[CH2:26]([N:33]1[C:37](=[O:38])[CH2:36][C:35]([C:44](=[O:46])[NH:54][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:34]1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 86751384HCID 86751384, compound

Product 1

HCID 22903655HCID 22903655, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Hydroxybenztriazole (2.78 g) and dicyclohexylcarbodiimide (42.5 g) were added to a mixture of monoethyl 1-benzyl-5-oxopyrrolidine-3,3-dicarboxylate (60.0 g), benzylamine (23.2 g) and tetrahydrofuran (500 ml), and the mixture was stirred at room temperature overnight. The insoluble matter was removed by filtration and the filtrate was concentrated. Ethyl acetate (400 ml) was added and the mixture was sequentially washed with an aqueous solution of potassium carbonate, water, dilute hydrochloric acid and saturated brine, dried, and concentrated to give 78 g of the object compound as white crystals, melting point 63°-65° C.

Workup

  1. customThe insoluble matter was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. additionEthyl acetate (400 ml) was added
  4. washthe mixture was sequentially washed with an aqueous solution of potassium carbonate, water, dilute hydrochloric acid and saturated brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4a379a635a0b4a66bb9f12e491c00d19
Source dataset
uspto-grants-1997_10
Patent number
US05677316

Reaction notes

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