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

HRID 1483967Notes

Reaction equation

HRID 1483967 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-620a24eca2644401ab90b5cbf7130053
Source dataset
uspto-grants-2016_08
Patent number
US09420814B2

Reaction notes

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