Potassium Carbonate → HCID 58266760, compound

HRID 1888418Notes

Reaction equation

HRID 1888418 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[CH3:10][C:11]1([CH3:17])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:14]2[CH2:15][CH2:16][C:11]([CH3:17])([CH3:10])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 1381004,4-Dimethylpiperidine

Product 1

HCID 58266760HCID 58266760, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-bromobenzyl bromide (500 mg, 2.0 mmol) and 4,4-dimethylpiperidine (249 mg, 2.2 mmol) and potassium carbonate (331 mg, 2.4 mmol) in acetonitrile (20 mL) was heated under reflux for 2 h. The reaction mixture was then cooled to ambient temperature and the reaction mixture concentrated under reduced pressure. The resultant oil was loaded onto an SCX-2 cartridge (10 g) and eluted with 2N ammonia in methanol to afford the title compound (323 mg, 57%). 1H NMR (CDCl3, 300 MHz): 7.42 (d, J=8.31 Hz, 2H), 7.19 (d, J=8.24 Hz, 2H), 3.44 (s, 2H), 2.35 (t, J=5.44 Hz, 4H), 1.37 (t, J=5.60 Hz, 4H), 0.90 (s, 6H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. concentrationthe reaction mixture concentrated under reduced pressure
  4. washeluted with 2N ammonia in methanol

Sources & evidence

ORD record
ord-6cd60f6503bc4dcda7485d65a521cde2
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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