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

HRID 2405976Notes

Reaction equation

HRID 2405976 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[H-].[Na+].[C:13]([O:17][C:18]([N:20]([CH2:24][CH2:25]Cl)[CH2:21][CH2:22]Cl)=[O:19])([CH3:16])([CH3:15])[CH3:14].N1(C#N)CCCCC1>CN(C=O)C>[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:25][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([C:9]#[N:10])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 73736PiperidinocarbonitrileHCID 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 6228DimethylformamideSolvent

Procedure

4-Chlorophenylacetonitrile was reacted with three equivalents of sodium hydride and one equivalent of N-tert-butyloxycarbonyl-bis-(2-chloroethyl)amine in DMF, initially at room temperature and then at 60° C. to give, after work up, the N-protected piperidine nitrile title compound.

Workup

  1. customat 60° C. to give

Sources & evidence

ORD record
ord-9a9191f4391d451583e6cc03ac2fde42
Source dataset
uspto-grants-2014_08
Patent number
US08809336B2

Reaction notes

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