Potassium Carbonate → HCID 58266488, compound

HRID 1505901Notes

Reaction equation

HRID 1505901 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])[O:16][CH2:15][CH2:14][NH: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:13]2[CH2:14][CH2:15][O:16][C:11]([CH3:17])([CH3:10])[CH2:12]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 189596742,2-Dimethylmorpholine

Product 1

HCID 58266488HCID 58266488, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-bromobenzyl bromide (1.5 g, 6.0 mmol), 2,2-dimethylmorpholine (0.69 g, 6.0 mmol) and potassium carbonate (0.99 g, 7.2 mmol) in acetonitrile (60 mL) was heated at 85° C. for 20 h. The mixture was allowed to cool to ambient temperature and the solid was removed by filtration and the filtrate evaporated. The resultant residue was dissolved in DCM/methanol and loaded onto a 20 g SCX-2 cartridge which was washed with methanol then 2N ammonia in methanol. Concentration of the combined basic fractions afforded the title compound (1.65 g, 97%) as an orange oil. 1H NMR (CDCl3, 300 MHz): 7.44 (d, J=8.0 Hz, 2H), 7.22 (d, J=8.0 Hz, 2H), 3.75 (t, J=4.8 Hz, 2H), 3.39 (s, 2H), 2.37 (t, J=4.6 Hz, 2H), 2.16 (s, 2H), 1.23 (s, 6H).

Workup

  1. temperatureto cool to ambient temperature
  2. customthe solid was removed by filtration
  3. customthe filtrate evaporated
  4. dissolutionThe resultant residue was dissolved in DCM/methanol
  5. washwas washed with methanol

Sources & evidence

ORD record
ord-781617929e784e0c84949a06d7647003
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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