Diethyl Ether → Cgp 29030A

HRID 1381881Notes

Reaction equation

HRID 1381881 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6]([Cl:8])=[O:7].[Cl:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1.C(OCC)C>C(Cl)Cl>[ClH:8].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][N:24]([C:6](=[O:7])[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=3)[CH2:23][CH2:22]2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 870033,5-Dimethoxybenzoyl chlorideHCID 122357141-[2-(4-Chlorophenyl)ethyl]piperazine

Product 1

HCID 3082655Cgp 29030A

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

71.9 g of 3,5-dimethoxybenzoyl chloride dissolved in 700 ml of CH2Cl2 are added at room temperature to a solution of 80.5 g of 1-(p-chlorophenethyl)-piperazine in 1200 ml of CH2Cl2. The rate of addition is so selected that the exothermic reaction remains under control. The whole is then stirred for 15 minutes under reflux and then for a further 1 hour at room temperature. After the addition of 1900 ml of diethyl ether, the whole is stirred for 15 minutes and then the resulting precipitate is filtered off with suction. The precipitate is dissolved in 3.3 litres of boiling ethanol. The colourless precipitate that is obtained after cooling to approximately 20° is filtered off with suction, washed with a little ethanol and dried under a high vacuum for 16 hours at 80°. 1-p-chlorophenethyl-4-(3,5-dimethoxybenzoyl)-piperazine hydrochloride having a melting point of 244°-246° (decomposition) is thus obtained.

Workup

  1. additionThe rate of addition
  2. customis so selected that the exothermic reaction
  3. temperatureunder reflux
  4. waitfor a further 1 hour at room temperature
  5. stirringthe whole is stirred for 15 minutes
  6. filtrationthe resulting precipitate is filtered off with suction
  7. dissolutionThe precipitate is dissolved in 3.3 litres of boiling ethanol
  8. customThe colourless precipitate that is obtained
  9. temperatureafter cooling to approximately 20°
  10. filtrationis filtered off with suction
  11. washwashed with a little ethanol
  12. customdried under a high vacuum for 16 hours at 80°

Sources & evidence

ORD record
ord-186f8a94b40b42ed9d5b6d05583679dc
Source dataset
uspto-grants-1989_02
Patent number
US04804661

Reaction notes

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