Benzenepropanal → HCID 86641454, compound

HRID 1189956Notes

Reaction equation

HRID 1189956 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([NH:5][CH2:6][CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=1)=[O:4].[C:20]1([CH2:26][CH2:27][CH:28]=O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCOC(C)=O>[F:1][C:2]([F:19])([F:18])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH2:28][CH2:27][CH2:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 7707BenzenepropanalHCID 86641451HCID 86641451, compound

Product 1

HCID 86641454HCID 86641454, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,2,2-trifluoro-N-(3-(3-nitrophenyl)allyl)acetamide (1.0 g, 3.6 mmol) and 3-phenylpropanal (0.48 g, 3.6 mmol) in EtOAc was degassed and saturated with argon. 10% Pd/C (500 mg) was added to this solution and the resulting mixture was stirred under H2 at 1 atm for 16 hrs, filtered through Celite, and concentrated under reduced pressure. Purification by flash chromatography (40% to 50% EtOAc—hexanes gradient) gave 2,2,2-trifluoro-N-(3-(3-(3-phenylpropylamino)phenyl)propyl)acetamide as a colorless semi-solid. Yield (0.54 g, 41%). 1H NMR (400 MHz, DMSO-d6) δ 9.41 (br.s, 1H), 7.30-7.17 (m, 5H) 6.95 (t, J=7.6 Hz, 1H), 6.36-6.34 (m, 3H), 5.50 (t, J=5.6 Hz, 1H), 3.18 (q, J=6.4 Hz, 2H), 2.98 (q, J=6.4 Hz, 2H), 2.67 (t, J=8.0 Hz, 2H), 2.43 (t, J=7.6 Hz, 2H), 1.82 (quintet, J=7.6 Hz, 2H), 1.73 (quintet, J=7.6 Hz, 2H).

Workup

  1. customwas degassed and saturated with argon
  2. addition10% Pd/C (500 mg) was added to this solution
  3. filtrationfiltered through Celite
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (40% to 50% EtOAc—hexanes gradient)

Sources & evidence

ORD record
ord-bc83b387b68249648f446b68d7836386
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

Loading…