Methylamine → (7-Bromo-5-fluoro-4H-1,3-benzodioxin-2-YL)-N-methylmethanamine

HRID 452460Notes

Reaction equation

HRID 452460 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:14])[C:5]2[CH2:10][O:9][CH:8]([CH2:11]Br)[O:7][C:6]=2[CH:13]=1.[CH3:15][NH2:16]>CCO>[Br:1][C:2]1[CH:3]=[C:4]([F:14])[C:5]2[CH2:10][O:9][CH:8]([CH2:11][NH:16][CH3:15])[O:7][C:6]=2[CH:13]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 671556997-bromo-2-(bromomethyl)-5-fluoro-4H-1,3-benzodioxine

Product 1

HCID 67155865(7-Bromo-5-fluoro-4H-1,3-benzodioxin-2-YL)-N-methylmethanamineYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation according to Example 12. 7-bromo-2-(bromomethyl)-5-fluoro-4H-1,3-benzodioxine (0.50 g, 1.53 mmol), methanamine (2.0 ml, 33% in EtOH) and EtOH (4.0 ml) were heated in a micro wave oven at 120° C. for 1 h 5 min. The volatiles were evaporated in vacuum and the crude product was chromathographed twice on a silica column using EtOAc/MeOH (4:1) as eluent. Collection of the fractions containing pure product and evaporation of the solvent afforded the title compound (0.40 g, 94%). 1H-NMR (400 MHz, MeOD): δ 6.93 (2H, m), δ 5.26 (1H, t, J 4.8 Hz), δ 4.93 (2H, dd, J1 18.4 Hz, J2 15.2 Hz), δ 3.02 (2H, m), δ 2.53 (3H, s) ppm.

Workup

  1. customPreparation
  2. customThe volatiles were evaporated in vacuum
  3. customCollection of the fractions
  4. additioncontaining pure
  5. customproduct and evaporation of the solvent

Sources & evidence

ORD record
ord-2389173add00426ea44527c95f60a60b
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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