Piperidine → HCID 54671175, compound

HRID 1842524Notes

Reaction equation

HRID 1842524 reaction equation
Cl[C:2]1[C:3]([N:8]2[CH2:11][CH:10]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=3)[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(N(CC)CC)C>CS(C)=O>[N:22]1([C:2]2[C:3]([N:8]3[CH2:11][CH:10]([C:12]4[CH:21]=[CH:20][C:19]5[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=5)[N:13]=4)[CH2:9]3)=[N:4][CH:5]=[CH:6][N:7]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 58548445HCID 58548445, compound

Product 1

HCID 54671175HCID 54671175, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 2-[1-(3-chloro-pyrazin-2-yl)-azetidin-3-yl]-quinoline (150 mg, 0.51 mmol) and piperidine (43.35 mg, 0.51 mmol) was added DMSO (2 mL) and triethylamine (0.05 g, 0.50 mmol). The solution was heated to 150° C. under microwave for 3 h. Then the mixture was extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (20 mL) and brine (60 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 60% EtOAc in hexanes) to give the title product (50 mg, 0.15 mmol, 28% yield) as a white solid.

Workup

  1. extractionThen the mixture was extracted with EtOAc (2×20 mL)
  2. washThe combined organic extracts were washed with water (20 mL) and brine (60 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel (20% to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-473870f42dc444f7b5fc5ec3c1681172
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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