Hydrochloric Acid → HCID 67195867, compound

HRID 2041687Notes

Reaction equation

[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[CH:7]([NH:27]C=O)[CH2:6][CH:5]1[CH3:30])(=[O:3])[CH3:2].Cl>C(O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH2:27])[CH2:6][C@@H:5]1[CH3:30])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

{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.

Workup

custommost of the ethanol was removed in vacuo
customthen partitioned between water (150 mL) and AcOEt (200 mL)
customThe layers were separated
extractionthe aqueous layer was extracted with AcOEt (5×100 mL)
dry with materialThe combined organic phases were dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-325b357128df43f28782f43073222e80
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580957B2

Reaction notes

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