Tosylmethyl isocyanide → HCID 45088250, compound

HRID 1523718Notes

Reaction equation

HRID 1523718 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.C1(C)C=CC(S([CH2:20][N+:21]#[C-])(=O)=O)=CC=1.CC(C)([O-])C.[K+]>COCCOC.C(O)C.[Cl-].[Na+].O.C(OCC)(=O)C>[CH:1]1([N:4]2[CH2:9][CH2:8][CH:7]([C:20]#[N:21])[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

Participants

8

Reactant 3

HCID 161915Tosylmethyl isocyanideHCID 162276291-Cyclopropylpiperidin-4-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 45088250HCID 45088250, compoundYield 41.2%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-cyclopropyl-4-piperidone (Alfa Aesar, 3.0 grams, 21.5 mmol) in a mixture of 1,2-dimethoxyethane (72 mL) and ethanol (2.2 mL) cooled at 0° C., was added p-toluenesulfonylmethylisocyanide (5.45 grams, 27.95 mmol). Solid potassium tertiary butoxide (5.54 grams, 49.45 mmol) was added over a period of 1 hour. The reaction mixture was stirred at this temperature for additional 1 hour and gradually warmed to room temperature. After stirring for 2 hours at this temperature, it was cooled to 0° C., diluted with brine and ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure to obtain crude product, which was purified by slica gel column to yield 1-cyclopropyl piperidine-4-carbonitrile (1.32 grams).

Workup

  1. temperaturegradually warmed to room temperature
  2. stirringAfter stirring for 2 hours at this temperature, it
  3. temperaturewas cooled to 0° C.
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulphate
  6. customthe solvent was removed under reduced pressure
  7. customto obtain crude product, which
  8. customwas purified by slica gel column

Sources & evidence

ORD record
ord-02f6f6e414da41df80533706831bbfa7
Source dataset
uspto-grants-2015_07
Patent number
US09079894B2

Reaction notes

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