Dichloromethane → N-(2-phenylpropyl)-4-(trifluoromethyl)benzamide

HRID 445288

Reaction equation

HRID 445288 reaction equation
Cl.[C:2]1([CH:8]([CH3:11])[CH2:9][NH2:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.C(N(CC)CC)C.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>CCOC(C)=O>[C:2]1([CH:8]([CH3:11])[CH2:9][NH:10][C:28](=[O:29])[C:27]2[CH:31]=[CH:32][C:24]([C:23]([F:22])([F:33])[F:34])=[CH:25][CH:26]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 893322-Phenylpropylamine hydrochloride

Product 1

HCID 24636638N-(2-phenylpropyl)-4-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A 250-mL round-bottomed flask was charged with 2-phenylpropan-1-amine hydrochloride (7.75 g, 45.1 mmol), DCM (75 mL) and cooled down to 0° C. Triethylamine (13.8 mL, 99.3 mmol) was added followed by slow addition of 4-(trifluoromethyl)benzoyl chloride (7.4 mL, 49.7 mmol). After the addition was completed the mixture was stirred at RT for 1 h, diluted with EtOAc, washed with 10% HCl, sat NaHCO3, sat NaCl and dried over Na2SO4. The white residue was recrystallized from ether:hexanes and the title compound was obtained as a white solid. MS (ESI, positive ion) m/z: 308 (M+H).

Workup

  1. additionAfter the addition
  2. washwashed with 10% HCl
  3. dry with materialdried over Na2SO4
  4. customThe white residue was recrystallized from ether

Sources & evidence

ORD record
ord-801955b86aca49c581d050bddbfffdf3
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Linked notes

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