Dimethylformamide → HCID 86668497, compound

HRID 1801444Notes

Reaction equation

HRID 1801444 reaction equation
[Cl:1][C:2]1[C:3](Cl)=N[CH:5]=[CH:6][N:7]=1.Cl.[CH3:10][C:11]1[CH:12]=[C:13]([CH:17]2[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]2)[CH:14]=[CH:15][CH:16]=1.[C:23]([O-])([O-])=O.[K+].[K+].CN(C=O)C>CCOC(C)=O>[Cl:1][C:2]1[C:3]([N:19]2[CH2:20][CH2:21][CH2:22][CH:17]([C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([CH3:10])[CH:12]=3)[CH2:18]2)=[CH:23][CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 785752,3-DichloropyrazineHCID 450738183-(3-Methylphenyl)piperidine--hydrogen chloride (1/1)

Product 1

HCID 86668497HCID 86668497, compoundYield 119%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Dichloropyrazine (100 mg, 0.454 mmol), 3-(3-methylphenyl)piperidine hydrochloride (85 mg, 0.454 mmol), and K2CO3 (157 mg, 1.136 mmol) were combined in a 25-mL round bottom flask with a stirbar. DMF (4.48 mL) was added, and the reaction mixture was heated to 50° C. for 4 h. The reaction mixture was diluted with EtOAc (20 mL), and washed sequentially with sat. aq. NaHCO3 (20 mL) and brine (20 mL). The combined organics were dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound as a brown gum (155 mg, 76%), which was used in the subsequent step without further purification. Data for H-1: LC/MS: rt=3.17 min, m/z (M+H)=288.15 found; 288.79 required.

Workup

  1. washwashed sequentially with sat. aq. NaHCO3 (20 mL) and brine (20 mL)
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2fed96ab65fd47339eee37430ee59189
Source dataset
uspto-grants-2013_01
Patent number
US08349830B2

Reaction notes

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