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

HRID 429874Notes

Reaction equation

HRID 429874 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-2f37a1000ff54a148f8fc8069f45c65a
Source dataset
uspto-grants-2001_11
Patent number
US06319932B1

Reaction notes

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