Sodium Carbonate → HCID 22248142, compound

HRID 914863Notes

Reaction equation

HRID 914863 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH:9]=O)=[N:5][CH:6]=[CH:7][N:8]=1.Cl.[O:12]1[C:16]2[C:17]([CH2:21][CH2:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=[CH:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.O1CCCC1>[O:12]1[C:16]2[C:17]([CH2:21][CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([CH2:9][C:4]4[C:3]([O:2][CH3:1])=[N:8][CH:7]=[CH:6][N:5]=4)[CH2:25][CH2:24]3)=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=[CH:13]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 158805973-Methoxypyrazine-2-carbaldehydeHCID 22247890HCID 22247890, compound

Product 1

HCID 22248142HCID 22248142, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 124 mg of 3-methoxypyrazine-2-carboxaldehyde and 200 mg of 4-[2-(benzofuran-7-yl)ethyl]piperidine hydrochloride to 3 ml of tetrahydrofuran, 238 mg of sodium triacetoxyborohydride was added and the mixture was stirred 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 water and saturated brine in that order 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 (218 mg, 82% yield).

Workup

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

Sources & evidence

ORD record
ord-61da3a69142643dfb91a7680059fe374
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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