Acetonitrile → ethyl N-[N-(4-cyanobenzoyl)carbamoyl]piperidin-4-yloxyacetate

HRID 1900913Notes

Reaction equation

HRID 1900913 reaction equation
C(O)(=O)C.[NH:5]1[CH2:10][CH2:9][CH:8]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7][CH2:6]1.[C:18]([C:20]1[CH:30]=[CH:29][C:23]([C:24]([N:26]=[C:27]=[O:28])=[O:25])=[CH:22][CH:21]=1)#[N:19].C(#N)C>C(N(CC)CC)C>[C:18]([C:20]1[CH:21]=[CH:22][C:23]([C:24]([NH:26][C:27]([N:5]2[CH2:6][CH2:7][CH:8]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:10]2)=[O:28])=[O:25])=[CH:29][CH:30]=1)#[N:19]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 149137394-Cyanobenzoyl isocyanateHCID 131719662Ethyl piperidin-4-yloxyacetate, acetate salt

Product 1

HCID 23369999ethyl N-[N-(4-cyanobenzoyl)carbamoyl]piperidin-4-yloxyacetateYield 54%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a similar manner to Example 1, starting material step (a), the product from step (b) (1.7 g), 4-cyanobenzoyl isocyanate (1.1 g), acetonitrile (100 ml total) and triethylamine (2.1 ml) were stirred at ambient temperature overnight. The mixture was evaporated and the residue was purified by column chromatography on silica eluting with 5% ethanol/dichloromethane to give ethyl N-[N-(4-cyanobenzoyl)carbamoyl]piperidin-4-yloxyacetate (1.24 g) as a pale yellow oil: NMR Spectrum (DMSO-d6) 1.21 (3H, t), 1.50 (2H, m), 1.87 (2H, m), 3.20 (2H, m), 3.67 (3H, m), 4.12 (2H, q), 4.15 (2H, s), 7.97 (4H, s), 10.40 (1H, br s); Mass Spectrum m/Z 360 (M+H)+.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography on silica eluting with 5% ethanol/dichloromethane

Sources & evidence

ORD record
ord-426687c57a754075954b9f49e75e6c70
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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