Sodium hydride → Tert-butyl 4-(2-chlorophenyl)-4-cyanopiperidine-1-carboxylate

HRID 581805Notes

Reaction equation

HRID 581805 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:12][CH2:13]Cl)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]#[N:24].[H-].[Na+]>C1COCC1.CN(C=O)C>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1([C:23]#[N:24])[CH2:2][CH2:3][N:4]([C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76112(o-Chlorophenyl)acetonitrileHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

Product 1

HCID 21712251Tert-butyl 4-(2-chlorophenyl)-4-cyanopiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

A solution of bis(2-chloroethyl)-N-(1,1-dimethylethoxy)carbonyl amine (9.298 g, 38.4 mmol) and 2-chlorophenylacetonitrile (5.0 g, 32.0 mmol) in a 4:1 mixture of THF/DMF (15 mL) was treated with NaH (2.82 g, 70.4 mmol) at 60 OC (7 d). The solvent was removed in vacuo, the residue dissolved in EtOAc (200 ml) and washed with saturated NaHCO3 (50 ml), H2O (2×50ml), and saturated aqueous NaCl (50 ml), dried Na2SO4) and concentrated in vacuo. Trituration of the residue with 100% MeOH afforded 4-(2-chlorophenyl)4-cyano-N-(1,1-dimethylethoxy) carbonyl piperidine as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in EtOAc (200 ml)
  3. washwashed with saturated NaHCO3 (50 ml), H2O (2×50ml), and saturated aqueous NaCl (50 ml), dried Na2SO4) and
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2880c4deeefb4fa4949f94178e64470e
Source dataset
uspto-grants-1999_07
Patent number
US05922722

Reaction notes

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