3-(Trifluoromethyl)benzylamine → HCID 19862162, compound

HRID 1961467Notes

Reaction equation

HRID 1961467 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].CC1(C)[O:19][C:18](=O)[CH:17]=[C:16]([CH3:21])[O:15]1>CCOC(C)=O>[O:15]=[C:16]([CH3:21])[CH2:17][C:18]([NH:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:4]=1)=[O:19]

Participants

4

Reactant 2

HCID 759623-(Trifluoromethyl)benzylamineHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

Product 1

HCID 19862162HCID 19862162, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

3-(Trifluoromethyl)benzylamine (2.0 ml, 13.95 mmol) was mixed with 2,2,6-trimethyl-4H-1,3-dioxin-4-one (2.0 ml, 15.12 mmol), The mixture was stirred at 150° C. for 2 hours followed by 60 hours at 50° C. The reaction was cooled, diluted with EtOAc (50 ml), washed with 1M HCl (40 ml), NaHCO3 (2*40 ml, sat aq), dried over MgSO4 and evaporated. The crude product was purified by precipitation from toluene/pet.ether to give 2.57 g (71%) of 3-oxo-N-(3-(trifluoromethyl)benzyl)butanamide as pale solids.

Workup

  1. waitfollowed by 60 hours at 50° C
  2. temperatureThe reaction was cooled
  3. washwashed with 1M HCl (40 ml), NaHCO3 (2*40 ml, sat aq)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe crude product was purified by precipitation from toluene/pet

Sources & evidence

ORD record
ord-8beb71b9a55e4ca6b1d35594feec661b
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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