Phenethylamine → HCID 44422393, compound

HRID 1352168Notes

Reaction equation

HRID 1352168 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([NH:11][CH:12]3[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[C:19]1([CH2:25][CH2:26][NH2:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.CO>CO>[CH:1]1[C:10]2[C:5](=[C:6]([NH:11][CH:12]3[CH2:17][CH2:16][CH:15]([NH:27][CH2:26][CH2:25][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:14][CH2:13]3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178381944-(5-Isoquinolylamino)-1-cyclohexanone2×HCID 21893726Hydrochloride methanol

Product 1

HCID 44422393HCID 44422393, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(5-Isoquinolylamino)-1-cyclohexanone (intermediate 4) (60 mg) and 2-phenylethylamine (61 mg) were dissolved in methanol (1 ml), and sodium triacetoxyborohydride (105 mg) was added by portions to the solution at room temperature. The reaction mixture was stirred at room temperature for 18 hr. Hydrochloric acid-methanol was then added thereto, and the reaction mixture was stirred and was then concentrated. The residue was purified by HPLC [0.5% aqueous trifluoroacetic acid solution/acetonitrile]. A saturated aqueous sodium hydrogencarbonate solution (2 ml) was then added to fractions containing respective compounds, followed by extraction with chloroform-propanol (3/1). The organic layers were dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure to give an anti-form compound (24 mg) and a syn-form compound (11 mg).

Workup

  1. stirringthe reaction mixture was stirred
  2. concentrationwas then concentrated
  3. customThe residue was purified by HPLC [0.5% aqueous trifluoroacetic acid solution/acetonitrile]
  4. additionA saturated aqueous sodium hydrogencarbonate solution (2 ml) was then added to fractions
  5. additioncontaining respective compounds
  6. extractionfollowed by extraction with chloroform-propanol (3/1)
  7. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  8. customthe solvent was removed by distillation under the reduced pressure

Sources & evidence

ORD record
ord-b4154b15397b4438a9f5e092d386178a
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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