Water → [1-(4-Isothiocyanato-phenyl)-piperidin-4-yl]-dimethyl-amine

HRID 1348564

Reaction equation

HRID 1348564 reaction equation
[CH3:1][N:2]([CH3:18])[CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[C:19](C1NC=CN=1)(C1NC=CN=1)=[S:20].O>CN(C=O)C>[N:15]([C:12]1[CH:13]=[CH:14][C:9]([N:6]2[CH2:7][CH2:8][CH:3]([N:2]([CH3:18])[CH3:1])[CH2:4][CH2:5]2)=[CH:10][CH:11]=1)=[C:19]=[S:20]

Participants

5

Reactant 3

HCID 962WaterHCID 11086151N,N-dimethyl-1-(4-nitrophenyl)piperidin-4-amineHCID 11412697Thiocarbonyl diimidazole

Product 1

HCID 21091577[1-(4-Isothiocyanato-phenyl)-piperidin-4-yl]-dimethyl-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethyl-[1-(4-nitro-phenyl)-piperidin-4-yl]-amine (Example 2, 1.1 g, 5.0 mmol) was dissolved in DMF (5 mL). To the stirred solution, thiocarbonyl diimidazole (Aldrich, 1.18 g, 90%, 6 mmol) was added and the solution was stirred at room temperature for 80 minutes. The mixture was poured into water and extracted with diethyl ether. The extract was dried with sodium sulfate and concentrated to give a pale yellow solid. 1.12 g, 85%. MS (m+H)+: 262.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe extract was dried with sodium sulfate
  3. concentrationconcentrated
  4. customto give a pale yellow solid

Sources & evidence

ORD record
ord-96af6633f0ff44f3afb9eaf504ffa333
Source dataset
uspto-grants-2007_05
Patent number
US07211576B2

Linked notes

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