3-Fluoropropan-1-amine → 3-Fluoro-N-{[5-fluoro-7-(methylsulfonyl)-4H-1,3-benzodioxin-2-YL]methyl}propan-1-amine

HRID 452439Notes

Reaction equation

HRID 452439 reaction equation
Cl.[F:2][CH2:3][CH2:4][CH2:5][NH2:6].Br[CH2:8][CH:9]1[O:14][C:13]2[CH:15]=[C:16]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:17]=[C:18]([F:19])[C:12]=2[CH2:11][O:10]1.FCCCN>>[F:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:8][CH:9]1[O:14][C:13]2[CH:15]=[C:16]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:17]=[C:18]([F:19])[C:12]=2[CH2:11][O:10]1

Participants

4

Reactant 3

HCID 100193-Fluoropropan-1-amineHCID 219074553-Fluoropropan-1-amine hydrochlorideHCID 668876212-(bromomethyl)-5-fluoro-7-(methylsulfonyl)-4H-1,3-benzodioxine

Product 1

HCID 444785353-Fluoro-N-{[5-fluoro-7-(methylsulfonyl)-4H-1,3-benzodioxin-2-YL]methyl}propan-1-amine

Procedure

3-Fluoropropan-1-amine HCl-salt (0.178 g, 1.52 mmol) was basified on a SCX-3 ion exchange column (TEA/MeOH). 2-(bromomethyl)-5-fluoro-7-(methylsulfonyl)-4H-1,3-benzodioxine (8.5 mg, 0.026 mmol) and 3-fluoropropan-1-amine (0.15 M in MeOH/TEA:4/1, 5 ml) was heated under microwave radiation at 120° C. for 1 h 20 min. ESIMS: m/z 322 (M+H)+.

Sources & evidence

ORD record
ord-bd4275d8c8a14980bb5729f4856e5f77
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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