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

HRID 967502Notes

Reaction equation

HRID 967502 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-9b1ad83be7f245918e45a75a3454c489
Source dataset
uspto-grants-2005_10
Patent number
US06953790B2

Reaction notes

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