Methanol → Methyl 3-[(1-benzylpiperidin-4-yl)amino]pyrazine-2-carboxylate

HRID 493586Notes

Reaction equation

HRID 493586 reaction equation
Br[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:5]=[CH:4][N:3]=1.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1.CO>CC(O)C.C(OCC)(=O)C>[CH2:19]([N:16]1[CH2:17][CH2:18][CH:13]([NH:12][C:2]2[C:7]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:5]=[CH:4][N:3]=2)[CH2:14][CH2:15]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 4158521-Benzyl-4-piperidylamineHCID 13318551Methyl 3-bromopyrazine-2-carboxylate

Product 1

HCID 22293191Methyl 3-[(1-benzylpiperidin-4-yl)amino]pyrazine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2-bromopyrazine-3-carboxylate (J. Med. Chem., 1969, 12, 285) (2.2 g, 10.1 mmol) and 4-amino-1-benzylpiperidine (2.0 g, 10.5 mmol) was refluxed in 2-propanol overnight. Thin layer chromatography (10% methanol in ethyl acetate) showed the reaction was complete. The solvent was evaporated, and the crude product dissolved in chloroform (100 mL), which was washed with saturated sodium carbonate solution (20 mL), and dried over magnesium sulfate. The title compound was obtained as a gum (3.8 g). MS 327 (M+1).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude product dissolved in chloroform (100 mL)
  3. washwhich was washed with saturated sodium carbonate solution (20 mL)
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-1506bb39d763418fbc36d71be7bb14f6
Source dataset
uspto-grants-2009_05
Patent number
US07534784B2

Reaction notes

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