Potassium Carbonate → 1-Propanamine, N-[2-[3-fluoro-5-(methylsulfonyl)phenoxy]ethyl]-

HRID 1468651Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:11]=1)[O:5][CH2:6][CH2:7][NH2:8].[CH3:16][C:17]1C=CC(S(OCCC)(=O)=O)=C[CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:11]=1)[O:5][CH2:6][CH2:7][NH:8][CH2:16][CH2:17][CH3:18]

Participants

Conditions

Temperature: 120 °C

Procedure

2-[3-Fluoro-5-(methylsulfonyl)phenoxy]ethanamine (0.3 g, 1.26 mmol), propyl 4-methylbenzenesulfonate D2 (1.04 ml, 12.76 mmol) and potassium carbonate (0.35 g, 2.52 mmol) in acetonitrile (10 ml). The mixture was heated under microwave radiation at 120° C. for 45 min. The reaction mixtures were cooled to room temperature, filtrated and pooled before the volatiles were evaporated. Purification by flash column chromatography (ethyl acetate/methanol, 1:0 to 1:1) gave the title compound (0.15 g, 44%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether. MS m/z (relative intensity, 70 eV) 277 (M+, 2), 248 (26), 138 (3), 94 (3), 74 (bp).

Workup

customThe reaction mixtures
temperaturewere cooled to room temperature
filtrationfiltrated
customwere evaporated
customPurification by flash column chromatography (ethyl acetate/methanol, 1:0 to 1:1)

Sources & evidence

ORD record: ord-25892f7a7495464f89d6c7f21208dcb5
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006227B2

Reaction notes

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