Methylamine → HCID 67421372, compound

HRID 1799159Notes

Reaction equation

HRID 1799159 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[N:12][C:13](Cl)=[CH:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.CN.C[CH2:20][N:21](CC)CC>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[N:12][C:13]([NH:21][CH3:20])=[CH:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 20145731(4-Chlorophenyl)(6-chloro-3-pyridinyl)methanone

Product 1

HCID 67421372HCID 67421372, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound B (23.4 g, 93.22 mmol), methylamine (88 mL, 932 mmol, 33% solution in ethanol) and Et3N (37.51 mL, 280 mmol) in EtOH (100 mL) was heated in a sealed tube at 80° C. for 3 h. EtOH was removed under reduced pressure and the residue was dissolved in DCM (150 mL), washed with water and brine. The organic layer was dried (Na2SO4), filtered and evaporated. The crude product was purified by triturating with diethyl ether to obtain 12.5 g (55%) of compound C as off-white solid.

Workup

  1. customEtOH was removed under reduced pressure
  2. dissolutionthe residue was dissolved in DCM (150 mL)
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified
  8. customby triturating with diethyl ether

Sources & evidence

ORD record
ord-bfb90942bd124b3b9257789a1d3750d5
Source dataset
uspto-grants-2013_01
Patent number
US08343996B2

Reaction notes

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