Sodium hydride → tert-Butyl 4-cyano-4-(3-methoxyphenyl)piperidine-1-carboxylate

HRID 2376648Notes

Reaction equation

HRID 2376648 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]#[N:13])[CH:8]=[CH:9][CH:10]=1.Cl[CH2:15][CH2:16][N:17]([CH2:25][CH2:26]Cl)[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21]>CS(C)=O.C1COCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:11]2([C:12]#[N:13])[CH2:26][CH2:25][N:17]([C:18]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:24])[CH2:16][CH2:15]2)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 88310(3-Methoxyphenyl)acetonitrileHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

Product 1

HCID 49760266tert-Butyl 4-cyano-4-(3-methoxyphenyl)piperidine-1-carboxylateYield 87.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

This compound is prepared by the procedure described in step A of preparation 1.8, from 16.3 g of sodium hydride at a concentration of 60% in oil in 400 ml of DMSO, 30 g of 3-methoxyphenylacetonitrile in 150 ml of THF and 47 g of tert-butyl bis(2-chloroethyl)carbamate in 100 ml of DMSO. This gives 54 g of the expected product.

Workup

  1. customThis compound is prepared by the procedure

Sources & evidence

ORD record
ord-b82e6cbf59f04591998062b2943afe79
Source dataset
uspto-grants-2008_12
Patent number
US07468368B2

Reaction notes

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