Morpholine → 3-nitro-4-valeramidobenzoic Acid Morpholide

HRID 1939288Notes

Reaction equation

HRID 1939288 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][C:14](=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18])[C:7]([OH:9])=O)([O-:3])=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[NH:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][C:14](=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18])[C:7]([N:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1)=[O:9])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 117776583-nitro-4-(pentanoylamino)benzoic Acid

Product 1

HCID 538887563-nitro-4-valeramidobenzoic Acid Morpholide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (800 ml), 3 -nitro-4-valeramidobenzoic acid ([1]-(11)-1) (20.0 g) was dissolved. Dicyclohexylcarbodiimide (17.1 g) and 1-hydroxybenzotriazole (11.2 g) were added to the solution, and the mixture was stirred at room temperature for 15 minutes. Morpholine (7.27 g) was further added to the solution. The mixture was stirred for 16 hours. After the insolubles were removed from the reaction solution, the solution was concentrated and dried. The crude product was dissolved in chloroform, and the insolubles were removed, and the solution was purified by silica gel column chromatography (Kieselgel 60=400 g, chloroform/methanol=30/1) to obtain the compound ([1]-(12)-1) (22.95 g) as yellow needle crystals.

Workup

  1. stirringThe mixture was stirred for 16 hours
  2. customAfter the insolubles were removed from the reaction solution
  3. concentrationthe solution was concentrated
  4. customdried
  5. dissolutionThe crude product was dissolved in chloroform
  6. customthe insolubles were removed
  7. customthe solution was purified by silica gel column chromatography (Kieselgel 60=400 g, chloroform/methanol=30/1)
  8. customto obtain the compound ([1]-(12)-1) (22.95 g) as yellow needle crystals

Sources & evidence

ORD record
ord-b6bb95ed191a4ecb8596110a2b2d0650
Source dataset
uspto-grants-1997_12
Patent number
US05696118

Reaction notes

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