Glutaric anhydride → HCID 70182291, compound

HRID 726433Notes

Reaction equation

HRID 726433 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]1(=[O:23])[O:22][C:20](=[O:21])[CH2:19][CH2:18][CH2:17]1.C(N(CC)CC)C.NCCCN1CCOCC1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 7940Glutaric anhydrideHCID 8471TriethylamineHCID 61055N-(3-Aminopropyl)morpholineHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 70182291HCID 70182291, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (1.46 g) obtained in the above (1) is dissolved in dichloromethane (20 ml), and thereto are added glutaric anhydride (0.86 g) and triethylamine (1.14 ml), and the mixture is stirred for two hours. To the mixture is added dropwise N-(3-aminopropyl)morpholine (0.3 ml), and the mixture is further stirred for 30 minutes. The mixture is evaporated under reduced pressure to remove the solvent, and thereto is added 10% aqueous citric acid solution, and extracted with ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate, and the desiccant is removed by filtration, and the filtrate is concentrated under reduced pressure to give the title compound (1.54 g).

Workup

  1. stirringthe mixture is further stirred for 30 minutes
  2. customThe mixture is evaporated under reduced pressure
  3. customto remove the solvent
  4. additionis added 10% aqueous citric acid solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  7. customthe desiccant is removed by filtration
  8. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-0e220cc9b8ad41a382f58e21e9645ccb
Source dataset
uspto-grants-1998_01
Patent number
US05707994

Reaction notes

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