3-Fluoropropan-1-amine → N-{[(2S)-5-Chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}-3-fluoropropan-1-amine

HRID 38956Notes

Reaction equation

HRID 38956 reaction equation
Cl.[F:2][CH2:3][CH2:4][CH2:5][NH2:6].CC1C=CC(S(O[CH2:18][C@@H:19]2[O:24][C:23]3[CH:25]=[C:26]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:27]=[C:28]([Cl:29])[C:22]=3[O:21][CH2:20]2)(=O)=O)=CC=1.FCCCN>>[Cl:29][C:28]1[C:22]2[O:21][CH2:20][C@H:19]([CH2:18][NH:6][CH2:5][CH2:4][CH2:3][F:2])[O:24][C:23]=2[CH:25]=[C:26]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:27]=1

Participants

4

Reactant 3

HCID 100193-Fluoropropan-1-amineHCID 219074553-Fluoropropan-1-amine hydrochlorideHCID 86652939[(2R)-5-chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 44468237N-{[(2S)-5-Chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}-3-fluoropropan-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). [(2R)-5-chloro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.027 g, 0.062 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. MS m/z (rel. intensity, 70 eV) 337 (M+, 0.4), 91 (5), 90 (bp), 85 (3), 70 (17), 63 (3).

Sources & evidence

ORD record
ord-4be9a84842ea48c4b2469a4316a3194c
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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