Phenethylamine → HCID 17683023, compound

HRID 445306Notes

Reaction equation

HRID 445306 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[F:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[F:29])[C:23](Cl)=[O:24]>C(Cl)Cl>[F:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[F:29])[C:23]([NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:24]

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 81531DiisopropylethylamineHCID 27245193,4-Difluorobenzoyl chloride

Product 1

HCID 17683023HCID 17683023, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of phenethylamine (1.01 mL, 7.95 mmol) and DIEA (1.38 mL, 7.95 mmol) in 20 mL of DCM, 3,4-difluorobenzoyl chloride (1.00 mL, 7.95 mmol) was added dropwise. The clear solution was stirred for 1 h. The reaction mixture was concentrated and the crude product was purified by silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound as a white solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.57 (ddd, J=10.63, 7.56, 2.12 Hz, 1H) 7.31-7.44 (m, 3H) 7.15-7.31 (m, 4H) 6.02 (br. s., 1H) 3.67-3.78 (m, 2H) 2.94 (t, J=6.87 Hz, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude product was purified by silica gel chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d9ba004027354b5aa6ca52bc59f43aa4
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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