Piperidine → HCID 58266540, compound

HRID 1888416Notes

Reaction equation

HRID 1888416 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[C:4]([O:10][CH3:11])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 534180344-Bromo-1-(chloromethyl)-2-methoxybenzene

Product 1

HCID 58266540HCID 58266540, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4-bromo-1-chloromethyl-2-methoxybenzene (1.50 g, 6.36 mmol) in acetonitrile (64 mL) was added potassium carbonate (1.05 g, 6.36 mmol) and piperidine (0.63 mL, 6.36 mmol) then the reaction mixture was heated under reflux for 15 h. The reaction mixture was cooled to ambient temperature and then filtered, the filtrate was then concentrated under reduced pressure to afford a residue that was then loaded onto an SCX-2 cartridge (10 g) and eluted with 2N ammonia in methanol to afford the title compound (1.73 g, 96%). 1H NMR (CDCl3, 300 MHz): 7.23 (d, J=8.1 Hz, 1H), 7.05 (dd, J=8.1, 1.9 Hz, 1H), 6.97 (d, J=1.9 Hz, 1H), 3.80 (s, 3H), 3.45 (s, 2H), 2.39 (t, J=5.0 Hz, 4H), 1.62-1.51 (m, 4H), 1.47-1.39 (m, 2H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 15 h
  3. filtrationfiltered
  4. concentrationthe filtrate was then concentrated under reduced pressure
  5. customto afford a residue that
  6. washeluted with 2N ammonia in methanol

Sources & evidence

ORD record
ord-7ec3df6a3ad24b90b42d88a258e30f3f
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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