3-Cyclohexene-1-carboxaldehyde → HCID 21098470, compound

HRID 1352134Notes

Reaction equation

HRID 1352134 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[CH:10](=O)[CH:11]1[CH2:16][CH:15]=[CH:14][CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:32][C:33]1[CH:34]=[C:35]2[C:39](=[CH:40][CH:41]=1)[NH:38][N:37]=[CH:36]2.C(=O)([O-])O.[Na+]>CO>[CH:11]1([CH2:10][N:3]2[CH2:8][CH2:7][CH:6]([NH:32][C:33]3[CH:34]=[C:35]4[C:39](=[CH:40][CH:41]=3)[NH:38][N:37]=[CH:36]4)[CH2:5][CH2:4]2)[CH2:16][CH2:15][CH2:14][CH:13]=[CH:12]1

Participants

7

Reactant 5

HCID 75083-Cyclohexene-1-carboxaldehydeHCID 880121H-Indazol-5-amineHCID 516892Sodium BicarbonateHCID 2723901PiperonylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21098470HCID 21098470, compoundYield 4.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Piperidone hydrochloride monohydrate (77 mg) and 1,2,3,6-tetrahydrobenzaldehyde (55 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. Further, 5-aminoindazole (54 mg) was added thereto, and the mixture was stirred for 30 min, followed by the addition of a 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 thereto, 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 (6 mg).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. additionfollowed by the addition of a 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-9ed57f7afb534a1589601eed6be74c2f
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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