Diisopropylethylamine → N-(6-Methoxypyridin-3-yl)-4-(2-methylphenoxy)piperidine-1-carbothioamide

HRID 222329Notes

Reaction equation

HRID 222329 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH3:11])=[N:8][CH:9]=1)=[C:2]=[S:3].Cl.[CH3:13][C:14]1[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=1[O:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(CC)C(C)C)(C)C>ClCCl>[CH3:11][O:10][C:7]1[N:8]=[CH:9][C:4]([NH:1][C:2]([N:20]2[CH2:21][CH2:22][CH:17]([O:16][C:15]3[CH:23]=[CH:24][CH:25]=[CH:26][C:14]=3[CH3:13])[CH2:18][CH2:19]2)=[S:3])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 126660255-Isothiocyanato-2-methoxypyridineHCID 171780564-(2-Methylphenoxy)piperidine hydrochloride

Product 1

HCID 57753857N-(6-Methoxypyridin-3-yl)-4-(2-methylphenoxy)piperidine-1-carbothioamideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Isothiocyanato-2-methoxypyridine [(829 mg, 4.99 mmol), J. Org. Chem. (1980), 45, 4219] was added to a solution of 4-(2-methylphenoxy)-piperidine hydrochloride [(990 mg, 4.3 mmol), J. Med. Chem. (1978), 21, 309] and N,N-diisopropylethylamine (0.79 mL, 4.7 mmol) in dichloromethane (10 mL) and the mixture was stirred for 3 hours at room temperature. The organic solution was then diluted with dichloromethane and washed with sodium hydrogen carbonate solution and brine. The organic solution was dried over magnesium sulfate and concentrated in vacuo. Trituration of the residue with diethyl ether afforded the title compound as a solid in 85% yield, 1.3 g. LRMS APCI m/z 358 [M+H]+

Workup

  1. washwashed with sodium hydrogen carbonate solution and brine
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46b40954c91f42c698693e3b1acca279
Source dataset
uspto-grants-2012_06
Patent number
US08207198B2

Reaction notes

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