Triethylamine → Methyl 4-(n-(phenylmethyl)-n-((2-bromophenyl)methyl) amino)but-2-enoate

HRID 1057479Notes

Reaction equation

HRID 1057479 reaction equation
BrC1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Br:18]C/C=C/C(OC)=O.C(N([CH2:31][CH3:32])CC)C.C[CH2:34][O:35][C:36]([CH3:38])=[O:37]>C(#N)C>[C:12]1([CH2:11][N:10]([CH2:31][CH:32]=[CH:38][C:36]([O:35][CH3:34])=[O:37])[CH2:9][C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[Br:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 53691752-Butenoic acid, 4-bromo-, methyl esterHCID 11055371N-benzyl-2-(2-bromophenyl)ethanamine

Product 1

HCID 69158924Methyl 4-(n-(phenylmethyl)-n-((2-bromophenyl)methyl) amino)but-2-enoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(2-(2-Bromophenyl)ethyl)-N-(phenylmethyl)amine was dissolved in acetonitrile (0.2 M), followed by addition of methyl 4-bromocrotonate (1.2 eq) and triethylamine (1.5 eq), and the reaction was refluxed overnight. After cooling to room temperature, the reaction was diluted with EtOAc, washed with 10% sodium carbonate, water, and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (silica; 50% EtOAc/Hex) afforded a colorless oil. EI-MS m/z 388/390 (M+H)+

Workup

  1. temperaturethe reaction was refluxed overnight
  2. washwashed with 10% sodium carbonate, water, and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customFlash chromatography (silica; 50% EtOAc/Hex) afforded a colorless oil

Sources & evidence

ORD record
ord-b686d2fb7a264a81b4fb5771c1ceec25
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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