Sodium methanethiolate → 1-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylthio)ethyl]piperidine

HRID 419618Notes

Reaction equation

I[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([N+:18]([O-:20])=[O:19])=[CH:12][C:11]=2[CH3:21])[CH2:6][CH2:5]1.[CH3:22][S-:23].[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:21][C:11]1[CH:12]=[C:13]([N+:18]([O-:20])=[O:19])[C:14]([O:16][CH3:17])=[CH:15][C:10]=1[N:7]1[CH2:8][CH2:9][CH:4]([CH2:3][CH2:2][S:23][CH3:22])[CH2:5][CH2:6]1

Participants

Conditions

Temperature: 50 °C

Procedure

To 4-(2-iodoethyl)-1-[2-methyl-5-(methyloxy)-4-nitrophenyl]piperidine (40.6 g, 100 mmol) was added sodium thiomethoxide (7.75 g, 111 mmol) and diluted with DMF (201 mL). The reaction was stirred at 50° C. overnight. The solution was diluted with EtOAc and washed with H2O. The organic layer was dried (MgSO4), filtered, and rotovapped down to provide the title compound of step H (33.5 g) which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 6.64 (s, 1H), 3.86 (s, 3H), 3.23 (d, J=12.1 Hz, 2H), 2.60-2.72 (m, 2H), 2.46-2.52 (m, 2H), 2.14 (s, 3H), 2.01 (s, 3H), 1.75 (d, J=12.1 Hz, 2H), 1.50 (t, J=5.7 Hz, 3H), 1.16-1.35 (m, 2H).

Workup

washwashed with H2O
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered

Sources & evidence

ORD record: ord-c373630ee1d94f779eb814d551025904
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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