Propylamine → N-[(7-bromo-5-fluoro-4H-1,3-benzodioxin-2-yl)methyl]propan-1-amine

HRID 452407Notes

Reaction equation

HRID 452407 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.[CH2:15]([NH2:18])[CH2:16][CH3:17]>CCO>[Br:1][C:2]1[CH:3]=[C:4]([F:14])[C:5]2[CH2:10][O:9][CH:8]([CH2:11][NH:18][CH2:15][CH2:16][CH3:17])[O:7][C:6]=2[CH:13]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 671556997-bromo-2-(bromomethyl)-5-fluoro-4H-1,3-benzodioxine

Product 1

HCID 44481627N-[(7-bromo-5-fluoro-4H-1,3-benzodioxin-2-yl)methyl]propan-1-amineYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation according to Example 3. 7-bromo-2-(bromomethyl)-5-fluoro-4H-1,3-benzodioxine (0.20 g, 0.60 mmol), propan-1-amine (1.0 ml, 12.2 mmol) and EtOH (3.0 ml)was heated at 130° C. for 20 min. Purification by flash column chromatography (EtOAc/MeOH 10:1) gave the title compound (0.15 g, 82%). The amine was converted into the oxalic acid salt and was crystallised with MeOH/DEE (0.17 g). M.p. 215° C. MS m/z (rel. intensity, 70 eV) 304 (M+, 3), 302 (M+, 3), 205 (10), 203 (10), 72 (bp).

Workup

  1. customPreparation
  2. customPurification by flash column chromatography (EtOAc/MeOH 10:1)

Sources & evidence

ORD record
ord-76b3e4ac0ccd41688dd5fd89082e1238
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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