Cesium carbonate → HCID 59756879, compound

HRID 2196598Notes

Reaction equation

HRID 2196598 reaction equation
Cl.Cl[CH2:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[N:7]=[CH:6][CH:5]=1.[NH:18]1[CH2:23][CH2:22][CH:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:15][O:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[O:16][CH3:17])[N:7]=[CH:6][CH:5]=[C:4]2[CH2:3][N:18]1[CH2:19][CH2:20][CH:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 7238334-(N-Boc-amino)piperidineHCID 68993386HCID 68993386, compound

Product 1

HCID 59756879HCID 59756879, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-(Chloromethyl)-6,7-dimethoxyquinoline hydrochloride (0.75 g, 2.74 mmol), tert-butyl piperidin-4-ylcarbamate (0.77 g, 3.84 mmol), and cesium carbonate (2.68 g, 8.23 mmol) were dissolved in DMF (14 mL) and heated to 80° C. while stirring. After 4 hours, the reaction was cooled, DMF was removed, and the compound was taken up in DCM (150 mL) and water (20 mL). The aqueous layer was extracted 2× with DCM (50 mL). The organics were washed with brine, dried with sodium sulfate, and concentrated to give the desired product tert-butyl 1-((6,7-dimethoxyquinolin-4-yl)methyl)piperidin-4-ylcarbamate (1.04 g, 2.60 mmol, 95% yield). MS (ESI pos. ion) m/z: 402.2 (MH+). Calc'd exact mass for C22H31N3O4: 401. 1HNMR (400 MHz, CDCl3): 8.64-8.65 (d, J=4.4 Hz, 1H), 7.58 (s, 1H), 7.42 (s, 1H), 7.23-7.24 (d, J=4.4 Hz, 1H), 4.57-4.59 (m, 1H), 4.03 (s, 3H), 4.01 (s, 3H), 3.83 (s, 2H), 2.82-2.85 (bd, J=11.6 Hz, 2H), 2.18-2.24 (bt, J=10.8 Hz, 2H), 1.92-1.95 (bd, J=12.4 Hz, 2H), 1.44 (s, 9H), 1.41-1.44 (m, 2H, overlapping).

Workup

  1. temperaturethe reaction was cooled
  2. customDMF was removed
  3. extractionThe aqueous layer was extracted 2× with DCM (50 mL)
  4. washThe organics were washed with brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f7845f08f3b244d1bae8522feb41465a
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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