Hydrochloric Acid → HCID 67195867, compound

Participants

Reaction Conditions

Reaction Steps

{1-Acetyl-2-methyl-6-[4-(1-piperidinylmethyl)phenyl]-1,2,3,4-tetrahydro-4-quinolinyl}formamide (for a preparation see Intermediate 15) (4.784 g, 11.80 mmol) was dissolved in ethanol (115 mL) and treated with HCl (5N in water, 7.08 ml, 35.4 mmol). The resulting mixture was stirred at 85° C. for 16 h, at room temperature for 16 h then most of the ethanol was removed in vacuo. The aqueous residue was basified to pH 9 with a saturated NaHCO3 aqueous solution (100 mL) then partitioned between water (150 mL) and AcOEt (200 mL). The layers were separated and the aqueous layer was extracted with AcOEt (5×100 mL). The combined organic phases were dried over Na2SO4 and concentrated in vacuo to give (cis)-1-acetyl-2-methyl-6-[4-(1-piperidinylmethyl)phenyl]-1,2,3,4-tetrahydro-4-quinolinamine (4.36 g, 10.62 mmol, 90%) as a pale yellow solid which was used in the next step without further purification.

Provenance & Evidence