Potassium Carbonate → 1-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine

HRID 419614Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7](F)[C:6]([CH3:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].[CH3:14][S:15]([CH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)(=[O:17])=[O:16].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.CCOC(C)=O>[CH3:10][C:6]1[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[N:23]1[CH2:24][CH2:25][CH:20]([CH2:19][CH2:18][S:15]([CH3:14])(=[O:17])=[O:16])[CH2:21][CH2:22]1

Participants

Conditions

Temperature: 100 °C

Procedure

To 1-fluoro-2-methyl-5-(methyloxy)-4-nitrobenzene (Example 113, Step B) (2.02 g, 10.9 mmol) and 4-[2-(methylsulfonyl)ethyl]piperidine (2.48 g, 13.0 mmol) in DMSO (75 mL) was added K2CO3 (5.26 g, 38.1 mmol). The mixture was stirred at 100° C. for 2 days. The mixture was diluted with EtOAc, washed with H2O (4×), and rotovapped down. The crude residue was taken up in DCM and dried (MgSO4), filtered, and concentrated. Purification by flash chromatography provided the title compound of Step D (3.26 g, 9.14 mmol, 84%). 1H NMR (400 MHz, DMSO-d6) δ 1.30 (q, J=11.0 Hz, 2H), 1.52 (br. s., 1H), 1.60-1.72 (m, 2H), 1.78 (d, J=12.1 Hz, 2H), 2.17 (s, 3H), 2.67 (t, J=11.6 Hz, 2H), 2.95 (s, 3H), 3.07-3.21 (m, 2H), 3.21-3.35 (m, 2H), 3.88 (s, 3H), 6.66 (s, 1H), 7.74 (s, 1H).

Workup

washwashed with H2O (4×)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customPurification by flash chromatography

Sources & evidence

ORD record: ord-562e7b5324d248e9ad3cc8e2b99317ce
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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