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

HRID 38980Notes

Reaction equation

HRID 38980 reaction equation
Cl.[F:2][CH2:3][CH2:4][CH2:5][NH2:6].CC1C=CC(S(O[CH2:18][CH:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:24][CH:25]=3)[O:20]2)(=O)=O)=CC=1.FCCCN>>[F:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:18][CH:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][C:23]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:24][CH:25]=2)[O:20]1

Participants

4

Reactant 3

HCID 100193-Fluoropropan-1-amineHCID 219074553-Fluoropropan-1-amine hydrochlorideHCID 86652940[7-(methylsulfonyl)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 444685173-Fluoro-N-{[7-(methylsulfonyl)-3,4-dihydro-2H-chromen-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). [7-(methylsulfonyl)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate (0.020 g, 0.0561 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) 301 (M+, 3), 131 (8), 91 (9), 90 (bp), 86 (18), 70 (18).

Sources & evidence

ORD record
ord-76ba167dc18c4653bdaf6dada8c73947
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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