Dichloromethane → HCID 12404423, compound

HRID 1614619Notes

Reaction equation

HRID 1614619 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].[C:5]([N:8]1[CH2:16][CH2:15][CH:11]([C:12](Cl)=[O:13])[CH2:10][CH2:9]1)(=[O:7])[CH3:6].[CH2:17]([Cl:19])Cl>C1C(Cl)=CC=C(Cl)C=1>[Cl:1][C:9]1[CH:10]=[C:11]([C:12]([CH:11]2[CH2:15][CH2:16][N:8]([C:5](=[O:7])[CH3:6])[CH2:9][CH2:10]2)=[O:13])[CH:15]=[CH:16][C:17]=1[Cl:19]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12404423HCID 12404423, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 46851,4-DichlorobenzeneSolvent

Procedure

To a slurry of 53.2 g (0.4 mol) of aluminum chloride in 80 mL of diclorobenzene was added portionwise 38.0 g (0.2 mol) of N-acetylisonipecotic acid chloride (by closed addition method) so as to maintain at 5°-10°. During the addition a total of 50 mL of methylene chloride was added as needed. After the addition was complete the mixture was allowed to come to room temperature and stirred for two days. The mixture was poured onto an excess of crushed ice. The aqueous mixture was extracted several times with chloroform. The collected extracts were dried over anhydrous sodium sulfate and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was triturated in isopropyl ether. The residue crystallized and 22 g (36.5%) of crude product was obtained. A 5-g sample was recrystallized from acetone-water after treatment with charcoal. After air-drying the off-white solid was recrystallized from isopropyl ether-methanol, mp 134°-136°.

Workup

  1. temperatureto maintain at 5°-10°
  2. additionwas added
  3. additionAfter the addition
  4. customto come to room temperature
  5. additionThe mixture was poured onto an excess of crushed ice
  6. extractionThe aqueous mixture was extracted several times with chloroform
  7. dry with materialThe collected extracts were dried over anhydrous sodium sulfate
  8. filtrationthe mixture was filtered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe residue was triturated in isopropyl ether
  11. customThe residue crystallized

Sources & evidence

ORD record
ord-7f69f5f2edff4bd6a50ed752bfd3f049
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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