Phenethylamine → HCID 68749184, compound

HRID 624213Notes

Reaction equation

HRID 624213 reaction equation
Cl[CH2:2]/[CH:3]=[CH:4]/[B:5]1[O:9][C:8]([CH3:11])([CH3:10])[C:7]([CH3:13])([CH3:12])[O:6]1.C(=O)([O-])[O-].[K+].[K+].[CH2:20](CN)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:29](#[N:31])C>C(OCC)(=O)C>[CH2:20]([N:31]([CH3:29])[CH2:2]/[CH:3]=[CH:4]/[B:5]1[O:9][C:8]([CH3:11])([CH3:10])[C:7]([CH3:13])([CH3:12])[O:6]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 118305003-Chloropropenyl-1-boronic acid pinacol ester

Product 1

HCID 68749184HCID 68749184, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 4 mL vial were mixed (E)-2-(3-chloroprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.195 ml, 0.988 mmol) and potassium carbonate (273 mg, 1.975 mmol) in anhydrous acetonitrile (2 ml). Benzylmethylamine (0.166 ml, 1.284 mmol) was added to this mixture, and the reaction was stirred vigorously overnight at room temperature. The reaction was diluted with ethyl acetate and washed with water and brine. The organic layer was dried with sodium sulfate, decanted, and concentrated to provide the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. customdecanted
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-52a80714df9e4ab98cf819df081d2c75
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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