Hydrochloric Acid → HCID 68279552, compound

HRID 525492Notes

Reaction equation

HRID 525492 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH2:19][N:20]1[CH2:25][CH2:24][CH2:23][CH:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:21]1)[CH:13]=[CH:12]2)(C(C)(C)C)(C)C.Cl.C([O-])(O)=O.[Na+]>CCO>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH2:19][N:20]1[CH2:25][CH2:24][CH2:23][CH:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:21]1)[CH:13]=[CH:12]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68279573HCID 68279573, compound

Product 1

HCID 68279552HCID 68279552, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 1-((6-((tert-butyldimethylsilyl)oxy)quinolin-2-yl)methyl)piperidine-3-carboxylate (240 mg, 0.56 mmol) in EtOH (30 mL) was added HCl (3 N, 1 mL) dropwise at 0° C. The reaction mixture was stirred at room temperature for 2 h. The mixture was neutralized with sat. NaHCO3 and the organic solvent were removed. Then the mixture was extracted with DCM (3×10 mL). The combined organic layer was washed with brine (10 mL), dried (Na2SO4) and concentrated to give ethyl 1-((6-hydroxyquinolin-2-yl)methyl)piperidine-3-carboxylate as a white solid, 120 mg, Y: 60%, ESI-MS (M+H)+: 315.2. 1H NMR (400 MHz, CDCl3) δ: 7.86 (d, J=8.8 Hz, 2H), 7.54 (d, J=8.8 Hz, 1H), 7.29 (dd, J=9.2, 2.4 Hz, 1H), 7.05 (d, J=2.0 Hz, 1H), 4.09 (q, J=6.4 Hz, 2H), 3.90 (ABq, J=21.6, 13.6 Hz, 2H), 3.12-3.09 (m, 1H), 2.89-2.86 (m, 1H), 2.70-2.68 (m, 1H), 2.49-2.44 (m, 1H), 2.31-2.26 (m, 1H), 1.95-1.92 (m, 1H), 1.75-1.70 (m, 2H), 1.50-1.48 (m, 1H), 1.20 (t, J=7.2 Hz, 3H).

Workup

  1. customthe organic solvent were removed
  2. extractionThen the mixture was extracted with DCM (3×10 mL)
  3. washThe combined organic layer was washed with brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-000c93d9c0974898816dd91539d2e124
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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