HCID 59511421, compound → HCID 59511436, compound

HRID 1159993Notes

Reaction equation

HRID 1159993 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][N:5]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=1)[C:6](=[O:11])[C:7]([F:10])([F:9])[F:8]>CC(O)C.[Pd]>[NH2:19][C:15]1[CH:14]=[C:13]([CH2:12][N:5]([CH2:4][CH2:3][N:2]([CH3:22])[CH3:1])[C:6](=[O:11])[C:7]([F:8])([F:9])[F:10])[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 59511421HCID 59511421, compound

Product 1

HCID 59511436HCID 59511436, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of N-[2-(dimethylamino)ethyl]-2,2,2-trifluoro-N-[(3-nitrophenyl)methyl]acetamide (204 mg, 0.64 mmol) in 2-propanol (15 mL) was added 10% palladium on carbon (20 mg). The reaction was stirred at rt under a hydrogen atmosphere (1 atm) for 17 h. The reaction mixture was filtered through Celite, adsorbed to silica, and purified by column chromatography to generate the title compound in 62% yield (115 mg, 0.40 mmol). 1H NMR (400 MHz, CDCl3): δ 7.10 (t, J=7.6 Hz, 1H), 6.68-6.70 (m, 2H), 6.58 (d, J=7.9 Hz, 1H), 3.76 (s, 2H), 2.75 (t, J=6.0 Hz, 2H), 2.49 (t, J=6.0 Hz, 2H), 2.24 (s, 6H). MS (ESI) m/z=290 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-1eb54dd65b0d4c8f95ab00b1ce121313
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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