Piperidine → HCID 69544513, compound

HRID 1368945Notes

Reaction equation

HRID 1368945 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:20])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])=[CH:7][CH:6]=1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>CC(C)=O>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][C:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:6][CH:7]=1)=[O:20]

Participants

4

Reactant 2

HCID 8082Piperidine2×HCID 22504505HCID 22504505, compound

Product 1

HCID 69544513HCID 69544513, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of 1-[4-(2-chloroethoxy)phenyl]-2-(2-chlorophenyl)ethanone (4 g, 13 mmol) and piperidine (5.8 g, 68 mmol) in 80% aqueous acetone (50 ml) is refluxed for 12 h. Additional portions of 0.3 g of piperidine are added three times in 4 h intervals to the mixture. The solvents are evaporated. Diethyl ether is added and the precipitated piperidine hydrochloride is filtered off. Diethyl ether is evaporated and the residual product is purified by flash chromatography (eluent toluenetriethylamine 9:1). The yield is 4.1 g, 89%.

Workup

  1. temperatureis refluxed for 12 h
  2. customThe solvents are evaporated
  3. additionDiethyl ether is added
  4. filtrationthe precipitated piperidine hydrochloride is filtered off
  5. customDiethyl ether is evaporated
  6. customthe residual product is purified by flash chromatography (eluent toluenetriethylamine 9:1)

Sources & evidence

ORD record
ord-6c4c633c60954e12bb22642a03ed0675
Source dataset
uspto-grants-2003_06
Patent number
US06576645B1

Reaction notes

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