Glutaric anhydride → HCID 70182291, compound

HRID 1004509Notes

Reaction equation

HRID 1004509 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-3c9953c2f8104ecc8a2facc975a2a133
Source dataset
uspto-grants-2000_04
Patent number
US06048854

Reaction notes

Loading…