Phenethylamine → HCID 706676, compound

HRID 445253Notes

Reaction equation

HRID 445253 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>C(Cl)Cl>[CH2:8]([NH:9][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:21]([C:20]([F:19])([F:30])[F:31])=[CH:22][CH:23]=1)[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 706676HCID 706676, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of phenylethylamine (14.0 g, 14.6 mL, 0.11 mol) and DIEA (20.1 mL, 0.11 mol in DCM (500 mL) at 0° C. was added 4-(trifluoromethyl)benzoyl chloride (17.2 mL, 0.11 mol) dropwise. After the addition was completed, the reaction mixture was stirred at 0° C. and warmed up itself to RT for 16 h. An off-white solid precipitated was observed. The off-white solid was collected by filtration. The solid was then washed with DCM (2×50 mL), and dried under vacuum to give the title compound as a white solid. MS (ESI, positive ion) m/z: 294 (M+H).

Workup

  1. additionAfter the addition
  2. temperaturewarmed up itself to RT for 16 h
  3. customAn off-white solid precipitated
  4. filtrationThe off-white solid was collected by filtration
  5. washThe solid was then washed with DCM (2×50 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-262fec37b98441058100eba360444e02
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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