Phenethyl bromide → HCID 131718211, compound

HRID 1655967Notes

Reaction equation

HRID 1655967 reaction equation
[ClH:1].[C:2]1([C:8]#[C:9][CH2:10][O:11][CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20](Br)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[ClH:1].[CH2:20]([N:17]1[CH2:18][CH2:19][CH:14]([CH2:13][CH2:12][O:11][CH2:10][C:9]#[C:8][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:15][CH2:16]1)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 70053702HCID 70053702, compound

Product 1

HCID 131718211HCID 131718211, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The amine salt (0.34 g, 1.4 mmol), phenethyl bromide (0.26 g, 1.4 mmol), and potassium carbonate (0.50 g) were heated at reflux in absolute ethanol (50 mL) for 48 hours. After cooling, the mixture was filtered and concentrated in vacuo. The crude product was purified by chromatography on silica gel, eluting with 10% methanol in chloroform, and concentrated in vacuo to yield a colorless oil (0.25 g, 51%). 1H NMR(300 MHz, CDCl3 /TMS, δ): 7.45-7.10(m,10H), 4.36(s,2H), 3.6(t,2H,J=6Hz), 3.04-1.20(m,15H).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by chromatography on silica gel
  5. washeluting with 10% methanol in chloroform
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c1dafa4695043dab16c78e5fa2bc3d9
Source dataset
uspto-grants-1993_10
Patent number
US05252586

Reaction notes

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