Ammonia → 2-(Methylsulfonyl)-6-(1-propylpiperidin-4-YL)aniline

HRID 1878947Notes

Reaction equation

F[C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]1.[NH3:21]>CO>[CH3:11][S:8]([C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]2)[C:2]=1[NH2:21])(=[O:10])=[O:9]

Participants

Conditions

Temperature: 160 °C

Procedure

4-[2-fluoro-3-(methylsulfonyl)phenyl]-1-propylpiperidine (0.45 g, 1.52 mmol) was dissolved in a solution of ammonia in methanol (7 M, 15 ml). The mixture was heated to 160° C. in a sealed tube under microwave radiation for 20 h. The solvent was evaporated and the crude product was purified on a preparative HPLC-system. Yield: 0.125 g (30%). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 232-233° C. MS m/z (relative intensity, 70 eV) 296 (M+, 22), 267 (bp), 224 (31), 130 (23) 117 (20).

Workup

customThe solvent was evaporated
customthe crude product was purified on a preparative HPLC-system
customrecrystallized from ethanol/diethyl ether

Sources & evidence

ORD record: ord-3a35aba387d74a0c9a35f07834345c57
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314126B2

Reaction notes

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