Allylamine → N-Allyl-4-trifluoromethoxy-benzamide

HRID 842929Notes

Reaction equation

HRID 842929 reaction equation
O.ON1C2C=CC=CC=2N=N1.[CH2:12]([NH2:15])[CH:13]=[CH2:14].[F:16][C:17]([F:29])([F:28])[O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[CH2:12]([NH:15][C:23](=[O:24])[C:22]1[CH:26]=[CH:27][C:19]([O:18][C:17]([F:16])([F:28])[F:29])=[CH:20][CH:21]=1)[CH:13]=[CH2:14]

Participants

6

Reactant 4

HCID 7853AllylamineHCID 676134-(Trifluoromethoxy)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 22616308N-Allyl-4-trifluoromethoxy-benzamideYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-hydroxybenzotriazole hydrate (5.4 g, 40 mmol), allyl amine (60 mmol), and 4-(trifluoromethoxy)benzoic acid (8.3 g, 40 mmol) in DMF (110 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide-HCl (11.5 g, 60 mmol) at R.T. After the reaction mixture was stirred for 2.5 hrs, the solution was partitioned between 10% citric acid and ether. The organic layer was washed with sat. aqueous sodium bicarbonate, dried (sodium sulfate), filtered, and concentrated. The residue was purified by silica gel chromatography (20% ether/hexanes) to yield the title compound (colorless solid 96%). 1H NMR (400 MHz, CDCl3) δ7.85 (d, J=7.1 Hz, 2 H, Ar), 7.28 (d, J=5.9 Hz, 2 H, Ar), 6.31 (s, 1 H, NH), 5.94 (m, 1 H, CH2CHCH2), 5.25 (dd,J=8.6, 7.1 Hz, 2 H, NHCH2CH), 4.10 (m, 2 H, CHCH2);

Workup

  1. customthe solution was partitioned between 10% citric acid and ether
  2. washThe organic layer was washed with sat. aqueous sodium bicarbonate
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (20% ether/hexanes)

Sources & evidence

ORD record
ord-6582508f685642c48bc67f8d671abfab
Source dataset
uspto-grants-2002_04
Patent number
US06376530B1

Reaction notes

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