3-Phenylprop-2-enoyl chloride → (E)-N-[[4-dimethylamino-4-(3-fluorophenyl)-1-methyl-cyclohexyl]-methyl]-3-phenylacrylamide

HRID 76939Notes

Reaction equation

HRID 76939 reaction equation
[NH2:1][CH2:2][C:3]1([CH3:19])[CH2:8][CH2:7][C:6]([N:16]([CH3:18])[CH3:17])([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[C:29](Cl)(=[O:38])[CH:30]=[CH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>ClCCl>[CH3:17][N:16]([CH3:18])[C:6]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[CH2:5][CH2:4][C:3]([CH2:2][NH:1][C:29](=[O:38])/[CH:30]=[CH:31]/[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([CH3:19])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 660233-Phenylprop-2-enoyl chlorideHCID 81531DiisopropylethylamineHCID 68632146[4-Aminomethyl-1-(3-fluorophenyl)-4-methyl-cyclohexyl]-dimethylamine

Product 1

HCID 44252681(E)-N-[[4-dimethylamino-4-(3-fluorophenyl)-1-methyl-cyclohexyl]-methyl]-3-phenylacrylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the title compound of step 4 (polar diastereomer) (250 mg, 0.94 mmol) and Hünig's base (169 μl, 1.0 mmol) in abs. dichloromethane (10 mL) was mixed with cinnamic acid chloride (166 mg 1.0 mmol) and stirred for 24 h at RT. The organic solution was washed with saturated NaHCO3 solution and saturated NaCl solution, dried over Na2SO4, concentrated to low volume in a vacuum and the remaining residue was purified by flash chromatography with ethyl acetate/MeOH 4:1.

Workup

  1. washThe organic solution was washed with saturated NaHCO3 solution and saturated NaCl solution
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to low volume in a vacuum
  4. customthe remaining residue was purified by flash chromatography with ethyl acetate/MeOH 4:1

Sources & evidence

ORD record
ord-d69a644c9c4e494c8a384d5ec2a7e6a5
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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