Dimethylformamide → HCID 24693813, compound

HRID 911631Notes

Reaction equation

HRID 911631 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:8]1[C:13]([C:14]#[N:15])=[CH:12][N:11]=[C:10](Cl)[CH:9]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>CCCCCC.CCOC(C)=O>[CH:1]1([NH:7][C:10]2[CH:9]=[CH:8][C:13]([C:14]#[N:15])=[CH:12][N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7965CyclohexylamineHCID 11430Potassium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 24693813HCID 24693813, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
120 °C

Procedure

Add cyclohexylamine (7.1 g, 72 mmol) to a mixture of 6-chloronicotinitrile (1 g, 7.2 mmol), potassium carbonate (3 g, 21.7 mmol), and anhydrous DMF (10 mL). Heat the mixture in a sealed flask at 120° C. for 1.5 h. Cool the reaction to ambient temperature, dilute with hexane/EtOAc (1:1, 100 mL) and wash the mixture with aqueous 5% sodium chloride (3×30 mL). Collect the organic layer and concentrate in vacuo to obtain the desired intermediate (1.4 g, 97%). GC-MS m/z: 201 (M+).

Workup

  1. temperatureCool
  2. customthe reaction to ambient temperature
  3. washwash the mixture with aqueous 5% sodium chloride (3×30 mL)
  4. customCollect the organic layer
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-08c6c2c0d9b34db785a96f8984c728f0
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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