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Sodium Bicarbonate → 1-(1-(2-(7-Methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl)piperidin-4-yl)-1H-indole-6-carboxamide

HRID 494945
Notes
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Reaction equation

HRID 494945 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[C:30]([CH2:31][CH:32]=O)=[C:29]2[C:24]([C:25](=[O:36])[CH2:26][C:27]([CH3:35])([CH3:34])[O:28]2)=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(O)(=O)C>[CH3:19][O:20][C:21]1[C:30]([CH2:31][CH2:32][N:1]2[CH2:2][CH2:3][CH:4]([N:7]3[C:15]4[C:10](=[CH:11][CH:12]=[C:13]([C:16]([NH2:18])=[O:17])[CH:14]=4)[CH:9]=[CH:8]3)[CH2:5][CH2:6]2)=[C:29]2[C:24]([C:25](=[O:36])[CH2:26][C:27]([CH3:35])([CH3:34])[O:28]2)=[CH:23][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57682772(7-Methoxy-2,2-dimethyl-4-oxochroman-8-yl)acetaldehydeHCID 576827861-(piperidin-4-yl)-1H-indole-6-carboxamide

Product 1

HCID 116772571-(1-(2-(7-Methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl)piperidin-4-yl)-1H-indole-6-carboxamideYield 93.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

120 mg of 1-(piperidin-4-yl)-1H-indole-6-carboxamide and 163 mg of (7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)acetaldehyde were dissolved in 10 ml of methylene chloride. Thereafter, 0.06 ml of acetic acid was added to the reaction solution, and the obtained mixture was then stirred at room temperature for 15 minutes. Thereafter, 157 mg of sodium triacetoxyborohydride was added to the reaction solution, and the obtained mixture was then stirred at room temperature for 1 hour. Thereafter, a saturated sodium bicarbonate aqueous solution was added to the reaction solution, followed by extraction with chloroform. The extract was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (methanol-ethyl acetate), followed by solidification with ethyl acetate, so as to obtain 220 mg of the subject compound.

Workup

  1. stirringthe obtained mixture was then stirred at room temperature for 1 hour
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (methanol-ethyl acetate)

Sources & evidence

ORD record
ord-3c2b93f24f674912b34e708dc15424bd
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07538123B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes