Cyclopropylacetonitrile → tert-Butyl 4-[cyano(cyclopropyl)methylidene]piperidine-1-carboxylate

HRID 521190Notes

Reaction equation

HRID 521190 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH:15]1([CH2:18][C:19]#[N:20])[CH2:17][CH2:16]1>C1COCC1>[C:19]([C:18]([CH:15]1[CH2:17][CH2:16]1)=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1)#[N:20]

Participants

4

Reactant 2

HCID 643447CyclopropylacetonitrileHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 86729356tert-Butyl 4-[cyano(cyclopropyl)methylidene]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-oxopiperidine-1-carboxylate (2.0 g, 10 mmol) and cyclopropylacetonitrile (0.97 g, 12 mmol) were dissolved in THF (20 mL), heated to reflux, and allowed to stir for 3 hours. The mixture was then cooled to ambient temperature and concentrated in vacuo. The residue was purified by MPLC on silica gel to afford the title compound as a white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by MPLC on silica gel

Sources & evidence

ORD record
ord-3f04dfb7b81c48468fef189307a7c8d2
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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