4-Chlorobenzoyl chloride → Methyl 4-[1-(4-chlorobenzoyl)-piperazin-4-ylmethyl]-benzoate

HRID 2290453

Reaction equation

HRID 2290453 reaction equation
[N:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>N1C=CC=CC=1>[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([N:4]2[CH2:5][CH2:6][N:1]([CH2:7][C:8]3[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=3)[CH2:2][CH2:3]2)=[O:24])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 7018627Methyl 4-[(piperazin-1-yl)methyl]benzoate

Product 1

HCID 54279459Methyl 4-[1-(4-chlorobenzoyl)-piperazin-4-ylmethyl]-benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 15.3 g. (50 mmole) methyl 4-(piperazin-1-ylmethyl)-benzoate and 175 ml. anhydrous pyridine, there is added dropwise, at 0°-5° C., 8.7 g. (50 mmole) 4-chlorobenzoyl chloride and the reaction mixture kept for a further hour at 0° to 5° C., then overnight at 20° C. The reaction mixture is stirred into ice water and the precipitated product is filtered off with suction, washed with water and dried to give 18.5 g. (quantitative) of the desired product; m.p. 134°-135° C.

Workup

  1. customovernight
  2. customat 20° C
  3. filtrationthe precipitated product is filtered off with suction
  4. washwashed with water
  5. customdried
  6. customto give 18.5 g

Sources & evidence

ORD record
ord-6dc8888c09b34dc5bb0d689ff177e249
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Linked notes

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