4-(Trifluoromethyl)benzylamine → HCID 18978654, compound

HRID 1507250Notes

Reaction equation

HRID 1507250 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[Br:13][CH:14]([CH2:18][CH2:19][Br:20])[C:15](Cl)=[O:16]>C(OCC)C.O>[Br:13][CH:14]([CH2:18][CH2:19][Br:20])[C:15]([NH:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:11])([F:12])[F:1])=[CH:8][CH:7]=1)=[O:16]

Participants

5

Reactant 2

HCID 768044-(Trifluoromethyl)benzylamineHCID 44131432,4-Dibromobutyryl chloride

Product 1

HCID 18978654HCID 18978654, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (4-(trifluoromethyl)phenyl)methanamine (3 g, 17 mmol) in diethyl ether (60 mL) under nitrogen at 0° C. was added 2,4-dibromobutanoyl chloride (2.3 mL, 17 mmol) and the reaction mixture was stirred for 1 h at rt. The mixture was then diluted with water and extracted with 200 mL of ethyl acetate. The organic layer was dried over Na2SO4, filtered, and evaporated under reduced pressure to afford 2,4-dibromo-N-(4-(trifluoromethyl)benzyl)-butanamide (6.5 g, 87%). LCMS (method F) RT 2.01 min, m/z 434.8, 483.8; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.39-2.47 (m, 2H) 3.50-3.67 (m, 2H) 4.41 (dd, J=13.05, 6.02 Hz, 2H) 4.59-4.64 (m, 1H) 7.49 (d, J=7.53 Hz, 2H) 7.71 (d, J=8.03 Hz, 2H) 9.06 (s, 1H).

Workup

  1. extractionextracted with 200 mL of ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-135957104b124d7fba6e89264a8ebc90
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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