Cesium carbonate → 1-Boc-4-cyano-4-(2-cyanophenyl)-piperidine

HRID 277760Notes

Reaction equation

HRID 277760 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].[C:15](#[N:25])[CH2:16][C:17]1[C:18](=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:19]#[N:20].C(=O)([O-])[O-].[Cs+].[Cs+]>CCOC(C)=O>[C:15]([C:16]1([C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[C:19]#[N:20])[CH2:13][CH2:12][N:4]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:3][CH2:2]1)#[N:25]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 773682-CyanobenzeneacetonitrileHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

Product 1

HCID 226259671-Boc-4-cyano-4-(2-cyanophenyl)-piperidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of bis(2-chloroethyl)-N-(1,1-dimethylethoxy)carbonyl amine (19 g, 78 mmol) and homophthalonitrile (8.6 g, 60 mmol) and cesium carbonate (79 g, 241 mmol) was stirred at 60° C. for 12 hours. The solution cooled to room temperature and diluted with 500 ml EtOAc and washed with saturated aqueous NaHSO4 and saturated aqueous NaCl. The solution was dried over Na2SO4, concentrated in vacuo, and purified by PCTLC (30% EtOAc in Hexane) to afforded 4-cyano-N-(1,1-dimethylethoxy)carbonyl-4-(2-cyanophenyl)piperidine as a yellow/orange oil.

Workup

  1. washwashed with saturated aqueous NaHSO4 and saturated aqueous NaCl
  2. dry with materialThe solution was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by PCTLC (30% EtOAc in Hexane)

Sources & evidence

ORD record
ord-c3396408fb62458cbd5caf6c19645584
Source dataset
uspto-grants-2002_03
Patent number
US06358959B1

Reaction notes

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