Sulfuric Acid → HCID 24259182, compound

HRID 1270640Notes

Reaction equation

HRID 1270640 reaction equation
[C-]#[N:2].[Na+].S(=O)(=O)(O)O.[C-]#N.[CH2:11]([C:13]([CH2:24][CH3:25])(O)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:12].[OH-].[Na+]>C(O)(=O)C>[CH2:11]([C:13]([NH2:2])([CH2:24][CH3:25])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:12]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 5975CyanideHCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 22640885HCID 22640885, compound

Product 1

HCID 24259182HCID 24259182, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

Powdered sodium cyanide (1.18 g, 24 mmol) was placed in a flask and covered with 5.5 mL of acetic acid. A mixture of sulfuric acid (3 mL) and acetic acid (2.75 mL) was cooled to 0° C. and then added to the cyanide suspension over a period of 3 minutes. The mixture was stirred for 30 minutes at room temperature, followed by the addition of 1,1-diethyl-2-(4-methoxyphenyl)ethanol (4.6 g, 22 mmol). The mixture was stirred overnight then poured into ice and sodium hydroxide. The product was extracted with ether, and the ether layer dried over anhydrous sodium sulfate, and concentrated. The residue was suspended in 20% sodium hydroxide and refluxed overnight under nitrogen. The reaction was cooled, diluted with water, and extracted with ether. The ether layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by reversed-phase HPLC (C-18 using 0.1% HCl acetonitrile as the elutant) to give 1.91 g of 1,1-diethyl-2-(4-methoxyphenyl)ethylamine.

Workup

  1. stirringThe mixture was stirred overnight
  2. extractionThe product was extracted with ether
  3. dry with materialthe ether layer dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. temperaturerefluxed overnight under nitrogen
  6. temperatureThe reaction was cooled
  7. additiondiluted with water
  8. extractionextracted with ether
  9. customThe ether layer was separated
  10. washwashed with saturated brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated
  13. customThe residue was purified by reversed-phase HPLC (C-18

Sources & evidence

ORD record
ord-a4c42e2ed7974f3e93fe3b2f9a23ebdb
Source dataset
uspto-grants-2007_04
Patent number
US07202261B2

Reaction notes

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