4-Chlorobenzoyl chloride → HCID 13135950, compound

HRID 2290444Notes

Reaction equation

HRID 2290444 reaction equation
Cl.[N:2]1([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>N1C=CC=CC=1>[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([N:5]2[CH2:4][CH2:3][N:2]([C:8]3[CH:9]=[CH:10][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:17][CH:18]=3)[CH2:7][CH2:6]2)=[O:25])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 13034649HCID 13034649, compound

Product 1

HCID 13135950HCID 13135950, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 13.5 g. (50 mmole) ethyl 4-(piperazin-1-yl)-benzoate hydrochloride and 130 ml. anhydrous pyridine are added, at 5°-10° C., 50 mmole 4-chlorobenzoyl chloride. The temperature is allowed to come to 20° C. and the reaction mixture is subsequently stirred for 6 hours at 40° C. After cooling, it is stirred into 400 ml. ice water, extracted twice with 250 ml. amounts of methylene chloride and the organic phase is dried with anhydrous sodium sulphate and evaporated in a vacuum. The residue is triturated with ligroin and recrystallised from 150 ml. ethanol to give 15.6 g. of the desired product as colourless crystals; m.p. 147°-150° C.

Workup

  1. additionTo a mixture of 13.5 g
  2. customto come to 20° C.
  3. temperatureAfter cooling
  4. stirringit is stirred into 400 ml
  5. extractionice water, extracted twice with 250 ml
  6. dry with materialamounts of methylene chloride and the organic phase is dried with anhydrous sodium sulphate
  7. customevaporated in a vacuum
  8. customThe residue is triturated with ligroin
  9. customrecrystallised from 150 ml
  10. customethanol to give 15.6 g

Sources & evidence

ORD record
ord-3c97000e14f1498cb7113bf28d44f496
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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