Ethyl isocyanate → 2-((2-cyano-3-nitrophenoxy)methyl)-N-ethylpiperidine-1-carboxamide

HRID 332977Notes

Reaction equation

HRID 332977 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][NH:16]2)[C:6]=1[C:7]#[N:8])([O-:4])=[O:3].C(N(CC)CC)C.[CH2:28]([N:30]=[C:31]=[O:32])[CH3:29]>C1COCC1.O>[C:7]([C:6]1[C:5]([N+:2]([O-:4])=[O:3])=[CH:12][CH:11]=[CH:10][C:9]=1[O:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]1[C:31]([NH:30][CH2:28][CH3:29])=[O:32])#[N:8]

Participants

6

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 867142982-Nitro-6-(piperidin-2-ylmethoxy)benzonitrile hydrochloride

Product 1

HCID 867142972-((2-cyano-3-nitrophenoxy)methyl)-N-ethylpiperidine-1-carboxamideYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-nitro-6-(piperidin-2-ylmethoxy)benzonitrile hydrochloride (Example 26d, 0.5 g, 1.68 mmol) in THF were added triethylamine (0.514 mL, 3.7 mmol) and ethylisocyanate (0.2 mL, 2.52 mmol) and the reaction mixture was stirred at room temperature under nitrogen for 3 hours. The solution was then diluted with water and extracted with EtOAc, the combined organic phases were washed with brine, dried over MgSO4, filtered and evaporated to give 2-((2-cyano-3-nitrophenoxy)methyl)-N-ethylpiperidine-1-carboxamide (0.485 g, 87%) which was used in the next step without further purification. MS 333 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-4a8fd92e93e244ca80b469d6f7211329
Source dataset
uspto-grants-2014_11
Patent number
US08877922B2

Reaction notes

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