Sodium Carbonate → 2-Methoxy-3-(4-(2-methylphenoxymethyl)piperidino]methyl-pyrazine

HRID 914857Notes

Reaction equation

HRID 914857 reaction equation
Cl.[CH3:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[CH3:17][O:18][C:19]1[C:20]([CH:25]=O)=[N:21][CH:22]=[CH:23][N:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C(OCC)(=O)C>[CH3:17][O:18][C:19]1[C:20]([CH2:25][N:10]2[CH2:11][CH2:12][CH:7]([CH2:6][O:5][C:4]3[CH:13]=[CH:14][CH:15]=[CH:16][C:3]=3[CH3:2])[CH2:8][CH2:9]2)=[N:21][CH:22]=[CH:23][N:24]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 158805973-Methoxypyrazine-2-carbaldehydeHCID 172329964-[(2-Methylphenoxy)methyl]piperidine hydrochloride

Product 1

HCID 101720282-Methoxy-3-(4-(2-methylphenoxymethyl)piperidino]methyl-pyrazineYield 87.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After suspending 200 mg of 4-(2-methylphenoxymethyl)piperidine hydrochloride in 5 ml of dichloromethane, 137 mg of 3-methoxypyrazine-2-carboxaldehyde [CAS No. 63874-90-8] and 264 mg of sodium triacetoxyborohydride were added while stirring, and the stirring was continued overnight at room temperature. Aqueous sodium carbonate solution was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (236 mg, 87% yield).

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9869ff5da6904f5ea29a8d3e034bbdcb
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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