Sodium Bicarbonate → 1-{1-[2-(2-methoxynaphthalen-1-yl)ethyl]piperidin-4-yl}-1H-indole-6-carboxamide

HRID 494962Notes

Reaction equation

HRID 494962 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]([NH2:18])=[O:17])[CH:14]=3)[CH:9]=[CH:8]2)[CH2:3][CH2:2]1.[CH3:19][O:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]=1[CH2:31][CH:32]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.C(O)(=O)C>[CH3:19][O:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]=1[CH2:31][CH2:32][N:1]1[CH2:2][CH2:3][CH:4]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]([NH2:18])=[O:17])[CH:14]=3)[CH:9]=[CH:8]2)[CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 544795532-(2-Methoxynaphthalen-1-yl)acetaldehydeHCID 576827861-(piperidin-4-yl)-1H-indole-6-carboxamide

Product 1

HCID 576829191-{1-[2-(2-methoxynaphthalen-1-yl)ethyl]piperidin-4-yl}-1H-indole-6-carboxamideYield 58.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

70 mg of 1-(piperidin-4-yl)-1H-indole-6-carboxamide and 115 mg of (2-methoxynaphthalen-1-yl)acetaldehyde were dissolved in 2 ml of tetrahydrofuran. Thereafter, 0.03 ml of acetic acid and 91 mg of sodium triacetoxyborohydride were added to the reaction solution, and the obtained mixture was then stirred at room temperature overnight. Thereafter, a saturated sodium bicarbonate aqueous solution was added to the reaction solution, and then extracted with chloroform. The extract was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-methanol), so as to obtain 72 mg of the subject compound.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate-methanol)

Sources & evidence

ORD record
ord-a5a77a2a480c4f4184c10240c3b3ee18
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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