3-{[2-(1,3-dioxolan-2-yl)ethyl]amino}-N,N-bis(3-methylbutyl)-4-nitrobenzamide → HCID 68792502, compound

HRID 1161004Notes

Reaction equation

HRID 1161004 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][NH:8][C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][C:27]=1[N+:28]([O-])=O)[C:12]([N:14]([CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13]>C(OCC)(=O)C.CO.[Pd]>[NH2:28][C:27]1[CH:26]=[CH:25][C:11]([C:12]([N:14]([CH2:15][CH2:16][CH:17]([CH3:18])[CH3:19])[CH2:20][CH2:21][CH:22]([CH3:23])[CH3:24])=[O:13])=[CH:10][C:9]=1[NH:8][CH2:7][CH2:6][CH:2]1[O:1][CH2:5][CH2:4][O:3]1

Participants

4

Reactant 1

HCID 687931973-{[2-(1,3-dioxolan-2-yl)ethyl]amino}-N,N-bis(3-methylbutyl)-4-nitrobenzamide

Product 1

HCID 68792502HCID 68792502, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
20 °C

Procedure

3-{[2-(1,3-dioxolan-2-yl)ethyl]amino}-N,N-bis(3-methylbutyl)-4-nitrobenzamide (2.4 g) in solution in a mixture of ethyl acetate/methanol 2:1 (100 ml), and 10% palladium on carbon (240 mg) are introduced into an autoclave. After stirring for 4 hours under a hydrogen atmosphere (3 bar) at a temperature of approximately 20° C., the catalyst is eliminated by filtration on celite and the filtrate is concentrated under reduced pressure at 40° C. in order to produce the expected compound in the form of an oil (2.02 g; 89% yield).

Workup

  1. additionare introduced into an autoclave
  2. filtrationthe catalyst is eliminated by filtration on celite
  3. concentrationthe filtrate is concentrated under reduced pressure at 40° C. in order

Sources & evidence

ORD record
ord-6e75acc3cd244817a777591cf16c0ae2
Source dataset
uspto-grants-2010_10
Patent number
US07816539B2

Reaction notes

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