4-Bromobenzylamine hydrochloride → HCID 178471668, compound

HRID 250132Notes

Reaction equation

HRID 250132 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.C[O-].[Na+].[CH2:14]([O:16][CH:17]([O:22][CH2:23][CH3:24])[C:18](=[NH:21])OC)[CH3:15]>CO>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:18](=[NH:21])[CH:17]([O:22][CH2:23][CH3:24])[O:16][CH2:14][CH3:15])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 27240964-Bromobenzylamine hydrochlorideHCID 10942334Sodium MethoxideHCID 17874536Methyl 2,2-diethoxyethanecarboximidate

Product 1

HCID 178471668HCID 178471668, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4-Bromophenyl)methanamine hydrochloride (2.359 g, 10.39 mmol) and sodium methoxide (2.376 mL, 10.39 mmol) were added to a solution of methyl 2,2-diethoxyacetimidate (3.35 g, 20.78 mmol) in methanol (10 ml). The cloudy mixture was heated at 70 C for 1.5 h and the resulting yellow mixture was concentrated. The residue was purified by silica gel with 100% ethyl acetate to give a yellow viscous oil (2.04 g, 62%). 1H NMR (400 MHz, CDCl3) δ ppm 7.47 (2H, d, J=8.56 Hz), 7.23 (2H, d, J=8.06 Hz), 6.76 (1H, br. s.), 5.31 (1H, br. s.), 4.94 (1H, br. s.), 4.45 (2H, br. s.), 3.47-3.77 (4H, m), 1.26 (6H, t, J=7.05 Hz). LCMS:R.T.=2.12; [M+2]+=317.2.

Workup

  1. temperatureThe cloudy mixture was heated at 70 C for 1.5 h
  2. concentrationthe resulting yellow mixture was concentrated
  3. customThe residue was purified by silica gel with 100% ethyl acetate

Sources & evidence

ORD record
ord-10c62fda7a1e4b6e859158afdcc96881
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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