Hydrochloric Acid → HCID 12572571, compound

HRID 1393647Notes

Reaction equation

HRID 1393647 reaction equation
[CH3:1][C:2]([N+:9]([O-:11])=[O:10])([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=O.Cl.CN(C)CCCN=C=NCC.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>ClCCl.O.C(N(CC)CC)C>[CH2:24]([NH:31][C:5](=[O:7])[CH2:4][CH2:3][C:2]([CH3:1])([N+:9]([O-:11])=[O:10])[CH3:8])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 316444-Methyl-4-nitropentanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 12572571HCID 12572571, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

The 4-methyl-4-nitropentanoic acid (4.3 g) obtained above was dissolved in dichloromethane, and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (6.1 g) and triethylamine (4.5 ml) were added thereto and stirred for 1 hour. Benzylamine (3.4 g) was added thereto and stirred for 1 day. Water was added to the reaction mixture which was then acidified by 2 N hydrochloric acid and extracted with chloroform. The organic phase was washed with a saturated sodium bicarbonate solution and a saturated saline solution and dried over sodium sulfate anhydrous. The resulting product was concentrated under reduced pressure, and the residue was purified by column chromatography (eluting solvent; ethyl acetate:n-hexane 1:1.5) to give N-benzyl-4-methyl-4-nitropentanoic acid amide (2.5 g, Y.:38%) as a colorless oil.

Workup

  1. stirringstirred for 1 day
  2. extractionextracted with chloroform
  3. washThe organic phase was washed with a saturated sodium bicarbonate solution
  4. dry with materiala saturated saline solution and dried over sodium sulfate anhydrous
  5. concentrationThe resulting product was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography (eluting solvent; ethyl acetate:n-hexane 1:1.5)

Sources & evidence

ORD record
ord-650ac2f0932449c8b2661c01bc13b2b8
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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