Propylamine → N-[(7-bromo-6-fluoro-4H-1,3-benzodioxin-2-yl)methyl]propan-1-amine

HRID 452410Notes

Reaction equation

HRID 452410 reaction equation
[Br:1][C:2]1[C:3]([F:14])=[CH:4][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[C:3]([F:14])=[CH:4][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 671557797-bromo-2-(bromomethyl)-6-fluoro-4H-1,3-benzodioxine

Product 1

HCID 44481630N-[(7-bromo-6-fluoro-4H-1,3-benzodioxin-2-yl)methyl]propan-1-amineYield 41.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation according to Example 3. 7-bromo-2-(bromomethyl)-6-fluoro-4H-1,3-benzodioxine (0.60 g, 1.84 mmol), propan-1-amine (1.0 ml, 12.2 mmol) and EtOH (3.0 ml) was Heated at 130° C. for 40 min. Twice purification by flash column chroma-tography (EtOAc) gave the pure title compound (0.23 g, 41%). The amine was converted into the hydrochloric acid salt and crystallized from EtOH/DEE. M.p. 182° C. MS m/z (rel. intensity, 70 eV) 305 (M+, 3), 303 (M+, 3), 205 (8), 203 (8), 96 (6), 95 (10), 72 (bp).

Workup

  1. customPreparation
  2. customTwice purification by flash column chroma-tography (EtOAc)

Sources & evidence

ORD record
ord-6129fb507da1432c835d431b9a314456
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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