2-Phenylpropanal → HCID 21098508, compound

HRID 1352133Notes

Reaction equation

HRID 1352133 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[C:10]1([CH:16]([CH3:19])[CH:17]=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:34][C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[NH:40][N:39]=[CH:38]2.C(=O)([O-])O.[Na+]>CO>[NH:40]1[C:41]2[C:37](=[CH:36][C:35]([NH:34][CH:6]3[CH2:7][CH2:8][N:3]([CH2:17][CH:16]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH3:19])[CH2:4][CH2:5]3)=[CH:43][CH:42]=2)[CH:38]=[N:39]1

Participants

7

Reactant 5

HCID 71462-PhenylpropanalHCID 880121H-Indazol-5-amineHCID 516892Sodium BicarbonateHCID 2723901PiperonylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21098508HCID 21098508, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Piperidone hydrochloride monohydrate (77 mg) and 2-phenylpropionaldehyde (68 mg) were dissolved in methanol (1 ml), and sodium triacetoxyborohydride (106 mg) was added to the solution. The reaction mixture was stirred at room temperature for 18 hr. 5-Aminoindazole (54 mg) was further added thereto, and the mixture was stirred for 30 min, followed by the addition of borane-pyridine complex (0.05 ml). The reaction mixture was stirred at room temperature for 18 hr. A saturated aqueous sodium hydrogencarbonate solution (1 ml) was then added, and the mixture was extracted with chloroform-propanol (3/1). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by HPLC [chloroform/methanol] to give the title compound (21 mg).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. additionfollowed by the addition of borane-pyridine complex (0.05 ml)
  3. stirringThe reaction mixture was stirred at room temperature for 18 hr
  4. extractionthe mixture was extracted with chloroform-propanol (3/1)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by HPLC [chloroform/methanol]

Sources & evidence

ORD record
ord-b0f3377ea5854dadae582d9e4eaddbbb
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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