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

HRID 1976600Notes

Reaction equation

HRID 1976600 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-dimethylethloxy)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-faf438533f324554aa5f04188dc3b2d3
Source dataset
uspto-grants-2001_05
Patent number
US06228870B1

Reaction notes

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