Piperazine Dihydrochloride → Methyl 4-[(piperazin-1-yl)methyl]benzoate

HRID 2290450

Reaction equation

HRID 2290450 reaction equation
O.O.O.O.O.O.[NH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.Cl.Cl.N1CCNCC1.Br[CH2:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1>CO>[N:7]1([CH2:22][C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 8893Piperazine DihydrochlorideHCID 120181Piperazine, hexahydrateHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 7018627Methyl 4-[(piperazin-1-yl)methyl]benzoateYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixtue of 38 g. (0.2 mole) piperazine hexahydrate, 28 g. (0.2 mole) piperazine dihydrochloride and 150 ml. methanol is mixed, while stirring at ambient temperature, with 45 g. (0.2 mole) methyl 4-bromomethylbenzoate. The reaction mixture is left to stand for 2 days and suction filtered from the precipitate. The clear solution is evaporated and the residue is recrystallised from ethanol to give 39 g. (64%) of the desired compound as a monohydrochloride; m.p. 226°-227° C.

Workup

  1. waitThe reaction mixture is left
  2. filtrationsuction filtered from the precipitate
  3. customThe clear solution is evaporated
  4. customthe residue is recrystallised from ethanol
  5. customto give 39 g

Sources & evidence

ORD record
ord-c2a1209efed14541a56982e6500c44bc
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Linked notes

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