Acetyl chloride → HCID 44467589, compound

HRID 404251Notes

Reaction equation

HRID 404251 reaction equation
[C:1]1([C:7]2[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])[CH:10]=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](Cl)(=[O:19])[CH3:18].C([O-])(O)=O.[Na+]>C1COCC1>[C:1]1([C:7]2[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[CH:10]=[N:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 58294079HCID 58294079, compound

Product 1

HCID 44467589HCID 44467589, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(5-phenyl-1H-imidazol-1-yl)butan-1-amine (0.278 mmol) in THF (3 mL) at 0° C. was added acetyl chloride (0.306 mmol) drop wise and the resulting white suspension was allowed to warm to rt and stir for 5 h. Saturated NaHCO3 (2 mL) was added and the aqueous phase was extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo to afford a yellowish oil. Preparative thin layer chromatography afforded the pure product as colorless oil (30 mg, 43% yield). 1H NMR: 1.36 (m, 2H), 1.60 (m, 2H), 1.91 (s, 3H), 2.38 (br s, 1H), 3.12 (m, 2H), 4.00 (t, 2H, J=7.1 Hz), 5.80 (br s, 1H), 7.04 (s, 1H), 7.32-7.46 (m, 5H), 7.55 (s, 1H).

Workup

  1. extractionthe aqueous phase was extracted with EtOAc (3×10 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto afford a yellowish oil

Sources & evidence

ORD record
ord-39c4f2e8da064875a09393eff51d9a8e
Source dataset
uspto-grants-2014_06
Patent number
US08748469B2

Reaction notes

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