Hydrochloric Acid → HCID 118076148, compound

HRID 1051733Notes

Reaction equation

HRID 1051733 reaction equation
Cl.[C:2]([N:5]1[C:14]2[C:9](=[C:10]([O:28][CH2:29][CH2:30][CH3:31])[C:11]([CH:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[CH:12][CH:13]=2)[CH2:8][CH2:7][C@@H:6]1[CH3:32])(=[O:4])[CH3:3]>O1CCOCC1.C(OCC)C>[CH3:32][C@H:6]1[CH2:7][CH2:8][C:9]2[C:14](=[CH:13][CH:12]=[C:11]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:10]=2[O:28][CH2:29][CH2:30][CH3:31])[N:5]1[C:2](=[O:4])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118076055HCID 118076055, compound

Product 1

HCID 118076148HCID 118076148, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of hydrogen chloride (4.0 N in 1,4-dioxane, 1.4 mL, 5.6 mmol) was added to a solution of (S)-tert-butyl 4-(1-acetyl-2-methyl-5-propoxy-1,2,3,4-tetrahydroquinolin-6-yl)piperidine-1-carboxylate (480 mg, 1.1 mmol) in 1,4-dioxane (3 mL). The reaction was stirred for 3 hours resulting in a white precipitate. The reaction solution was diluted with diethyl ether (10 mL) and the precipitate was collected by filtration. The filtrate was further washed with diethyl ether (10 mL), collected and dried in vacuo affording the hydrochloride salt of the title compound as a white powder. The salt was free based via neutralization in ethyl acetate with saturated aqueous sodium carbonate solution until a pH=7.5 was achieved. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo affording (S)-1-(2-methyl-6-(piperidin-4-yl)-5-propoxy-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one (356 mg, 97%) as a colorless solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.96-1.06 (m, 6H), 1.11-1.26 (m, 1H), 1.38-1.61 (m, 4H), 1.66-1.89 (m, 2H), 2.20 (s, 3H), 2.16-2.28 (m, 2H), 2.52 (m, 2H), 2.67-2.80 (m, 2H), 2.83-2.94 (m, 1H), 2.99 (br d, J=12.02 Hz, 2H), 3.58-3.72 (m, 2H), 4.40-4.63 (br d, J=6.75 Hz, 1H), 7.03 (br s, 2H). MS (ESI, pos. ion) m/z 331 [M+H]+.

Workup

  1. customresulting in a white precipitate
  2. filtrationthe precipitate was collected by filtration
  3. washThe filtrate was further washed with diethyl ether (10 mL)
  4. customcollected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8afff9515d724bce82296203997d9524
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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