Water → HCID 22993572, compound

HRID 2304572Notes

Reaction equation

HRID 2304572 reaction equation
[C:1]([CH:3]([CH3:19])[CH2:4][N:5]1[CH2:10][CH2:9][C:8]([C:17]#[N:18])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[NH2:2][CH2:1][CH:3]([CH3:19])[CH2:4][N:5]1[CH2:6][CH2:7][C:8]([C:17]#[N:18])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 131723441HCID 131723441, compound

Product 1

HCID 22993572HCID 22993572, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of (+/−)-1-(2-cyanopropyl)-4-cyano-4-phenyl-piperidine (1.75 g, 6.91 mmol) in tetrahydrofuran (12 mL) was cooled to −78° C. and 1 M lithium aluminum hydride in tetrahydrofuran (3.9 ml) was added via syringe. The solution was warmed to −20° C. and after 4.5 hours, the reaction was worked up by sequential addition of water (0.20 mL), 2 M sodium hydroxide(0.40 mL), and water (0.20 mL). The reaction was then warmed to room temperature and diluted with ethyl acetate. The organic layer was washed with aq. sodium hydroxide and brine and dried over sodium sulfate. The filtered organic extract was concentrated to give an oil which was used without further purification.

Workup

  1. temperatureThe reaction was then warmed to room temperature
  2. washThe organic layer was washed with aq. sodium hydroxide and brine
  3. dry with materialdried over sodium sulfate
  4. extractionThe filtered organic extract
  5. concentrationwas concentrated
  6. customto give an oil which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-b117bda09891446f96a260276f7bfd3d
Source dataset
uspto-grants-2002_08
Patent number
US06436962B1

Reaction notes

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