Hydrochloric Acid → HCID 13151844, compound

HRID 1448975Notes

Reaction equation

HRID 1448975 reaction equation
N([O-])=O.[Na+].[C:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][C:15]=2N)[CH2:10][CH2:9]1)(=[O:7])[CH3:6].[ClH:24]>O>[C:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][C:15]=2[Cl:24])[CH2:10][CH2:9]1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 13151842HCID 13151842, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13151844HCID 13151844, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A solution of 4.5 g of sodium nitrite in 10 ml of water is added dropwise at 0°, with stirring, to a suspension of 16 g of N-acetyl-4-(2-amino-4-acetyl-phenyl)-piperidine in 75 ml of concentrated hydrochloric acid and 75 ml of water; stirring is continued at 0° for 2 hours; the reaction solution, which is now clear, is transferred to a dropping funnel precooled to 0°, and is slowly added dropwise to a solution, cooled to 0° and being stirred, of 16 g of copper-I-chloride in 150 ml of semi-concentrated hydrochloric acid. Stirring is maintained at 15° until the evolution of nitrogen has ceased (about 1 hour). An addition of 300 ml of water is made, and extraction is performed three times with 150 ml of ethyl acetate each time. The organic phases are extracted three times at 0° with 150 ml of 2 N sodium hydroxide solution each time; they are then cleared by filtration, washed neutral, dried over sodium sulphate and concentrated in vacuo. The oily N-acetyl-4-(2-chloro-4-acetyl-phenyl)-piperidine obtained in this manner can be used without purification.

Workup

  1. customis transferred to a dropping funnel
  2. customprecooled to 0°
  3. additionis slowly added dropwise to a solution
  4. temperaturecooled to 0°
  5. stirringStirring
  6. temperatureis maintained at 15° until the evolution of nitrogen
  7. custom(about 1 hour)
  8. extractionextraction
  9. extractionThe organic phases are extracted three times at 0° with 150 ml of 2 N sodium hydroxide solution each time
  10. filtrationthey are then cleared by filtration
  11. washwashed neutral
  12. dry with materialdried over sodium sulphate
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca0d36bf355a454e9e35a3c9edc6adcb
Source dataset
uspto-grants-1980_02
Patent number
US04188396

Reaction notes

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