Water → 2-Bromo-N-(2,4-dimethoxybenzyl)prop-2-en-1-amine

HRID 14384

Reaction equation

HRID 14384 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:12]=1[CH2:13][NH2:14].[Br:21][C:22]([CH2:24]Br)=[CH2:23].O>ClCCl>[Br:21][C:22](=[CH2:23])[CH2:24][NH:14][CH2:13][C:12]1[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:11]=1[O:10][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 105522,3-DibromopropeneHCID 30843432,4-Dimethoxybenzylamine hydrochloride

Product 1

HCID 222932192-Bromo-N-(2,4-dimethoxybenzyl)prop-2-en-1-amineYield 50.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (16.0 mL, 114 mmol) was added to a solution of 2,4-dimethoxybenzylamine hydrochloride (11.1 g, 54.5 mmol) and 2,3-dibromopropene (10.9 g, 54.5 mmol) in dichloromethane (200 mL). After 18 h, water was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography [100% dichloromethane→95% dichloromethane/5% (10% ammonium hydroxide/methanol)] gave the title compound (7.85 g).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×)
  2. washThe combined organic extracts were washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography [100% dichloromethane→95% dichloromethane/5% (10% ammonium hydroxide/methanol)]

Sources & evidence

ORD record
ord-f49580ace8ad45449d276d0cc5d02c55
Source dataset
uspto-grants-2010_06
Patent number
US07732438B2

Linked notes

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