Sodium hydride → tert-Butyl 4-(4-chlorophenyl)-4-cyanopiperidine-1-carboxylate

HRID 2376642Notes

Reaction equation

HRID 2376642 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.Cl[CH2:14][CH2:15][N:16]([CH2:24][CH2:25]Cl)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].[Cl-].[NH4+]>C1COCC1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:11]#[N:12])[CH2:25][CH2:24][N:16]([C:17]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:23])[CH2:15][CH2:14]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2415824-Chlorobenzyl cyanideHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

Product 1

HCID 49760270tert-Butyl 4-(4-chlorophenyl)-4-cyanopiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4.4 g of sodium hydride at a concentration of 60% in oil in 300 ml of THF is admixed rapidly at AT with 7.51 g of 4-chlorophenylacetonitrile and then with 12 g of tert-butyl bis(2-chloroethyl)carbamate, heated at 40° C. for 28 hours and then left with stirring at AT overnight. Saturated ammonium chloride solution is added to the reaction mixture, which is then concentrated under vacuum to remove the THF, after which the aqueous phase which remains is extracted with ether, the organic phase is washed with a buffer solution pH=2 and with saturated NaCl solution and dried over Na2SO4 and the solvent is evaporated under vacuum. This gives 12 g of the expected product, which is used as it is.

Workup

  1. waitleft
  2. concentrationis then concentrated under vacuum
  3. customto remove the THF
  4. extractionafter which the aqueous phase which remains is extracted with ether
  5. washthe organic phase is washed with a buffer solution pH=2 and with saturated NaCl solution
  6. dry with materialdried over Na2SO4
  7. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-d6760b9aa4c8480986eb286f5f43c1bd
Source dataset
uspto-grants-2008_12
Patent number
US07468368B2

Reaction notes

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