Hydrochloric Acid → HCID 67193937, compound

HRID 2366826Notes

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[CH2:30][CH3:31])(=[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[CH2:30][CH3:31])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

{1-acetyl-2-ethyl-6-[4-(1-piperidinylmethyl)phenyl]-1,2,3,4-tetrahydro-4-quinolinyl}formamide (for a preparation see Intermediate 6) (1.00 g, 2.026 mmol) was dissolved in Ethanol (20 ml), mixed with 5M hydrochloric acid (1.216 ml, 6.08 mmol) and stirred under reflux at 85° C. for 24 hours. The mixture was loaded onto a 5 g SCX-column, eluting with MeOH (70 mL), followed by 2M MeOH/NH3 (70 mL). Product-containing fractions were evaporated to dryness to give a yellow solid (1.242 g). The residue was purified on a 40+S Biotage silica column, eluting with DCM:2M MeOH/NH3 (1:0 to 19:1). Product-containing fractions were evaporated to dryness to give a pale yellow solid (0.782 g). LCMS (Method C): Rt 0.57, MH+=392

Workup

washeluting with MeOH (70 mL)
customProduct-containing fractions were evaporated to dryness

Sources & evidence

ORD record: ord-64047b15edfb483b900635296e77447b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697725B2

Reaction notes

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