Sodium hydride → tert-Butyl 4-(3-chlorophenyl)-4-cyanopiperidine-1-carboxylate

HRID 2376647Notes

Reaction equation

HRID 2376647 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[CH:8][CH:9]=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]>CS(C)=O.C1COCC1>[C:19]([O:18][C:17]([N:16]1[CH2:24][CH2:25][C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[CH:5]=2)([C:11]#[N:12])[CH2:14][CH2:15]1)=[O:23])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 73722m-ChlorophenylacetonitrileHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

Product 1

HCID 49760302tert-Butyl 4-(3-chlorophenyl)-4-cyanopiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 15.8 g of sodium hydride of a concentration of 60% in oil in 400 ml of DMSO is admixed dropwise at AT under an inert atmosphere with a solution of 30 g of 3-chlorophenylacetonitrile in 200 ml of THF and then with a solution of 45.5 g of tert-butyl bis(2-chloroethyl)carbamate in 200 ml of DMSO and is heated at 60° C. overnight. The reaction mixture is poured into an ice/water mixture and extracted with ether, the organic phase is washed with water and dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, eluting with DCM. This gives 33 g of the expected product.

Workup

  1. extractionextracted with ether
  2. washthe organic phase is washed with water
  3. dry with materialdried over Na2SO4
  4. customthe solvent is evaporated under vacuum
  5. customThe residue is chromatographed on silica gel
  6. washeluting with DCM

Sources & evidence

ORD record
ord-a29898ac28494aeead4771172a138aa1
Source dataset
uspto-grants-2008_12
Patent number
US07468368B2

Reaction notes

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