Piperidine → HCID 69544513, compound

HRID 1813944Notes

Reaction equation

HRID 1813944 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 toluene:triethylamine 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 toluene:triethylamine 9:1)

Sources & evidence

ORD record
ord-b060d74f55194bfcbcef1cd67f3ba61d
Source dataset
uspto-grants-2005_04
Patent number
US06875775B2

Reaction notes

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