Benzylamine → HCID 66718451, compound

HRID 515469Notes

Reaction equation

HRID 515469 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CO>[CH2:14]([NH:21][CH2:13][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:9]([O:11][CH3:12])=[O:10])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 10988417HCID 10988417, compound

Product 1

HCID 66718451HCID 66718451, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(4-bromophenyl)acrylate (8.2 g, 34 mmol) in methanol (100 mL) at room temperature was added benzylamine (3.7 mL, 34 mmol). The resulting mixture was stirred for 2 days and concentrated. The residue was purified by flash column chromatography on silica gel (chloroform/methanol=90/10 as an eluant) to yield methyl 3-benzylamino-2-(4-bromophenyl)propionate (7.1 g, 20.5 mmol, 60%) as a colorless oil.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash column chromatography on silica gel (chloroform/methanol=90/10 as an eluant)

Sources & evidence

ORD record
ord-15bfca47571c45cc8d3f5bc1788c7fe2
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

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