1-Piperazinecarboxylic acid, ethyl ester → HCID 14987925, compound

HRID 1494267Notes

Reaction equation

HRID 1494267 reaction equation
[N:1]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][N:14]=1>C1(C)C(C)=CC=CC=1>[CH2:10]([O:9][C:7]([N:1]1[CH2:6][CH2:5][N:4]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][N:14]=2)[CH2:3][CH2:2]1)=[O:8])[CH3:11]

Participants

4

Reactant 2

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 792226-Chloronicotinic acid

Product 1

HCID 14987925HCID 14987925, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 10.1 g of ethyl 1-piperazine carboxylate, 5.0 g of 6-chloronicotinic acid and 15 ml of xylene was stirred at 140°-150° C. for 3 hours. After cooled crystals were filtered, to the crystals was added a solution of 2.6 g of sodium hydroxide in 30 ml of water followed by extraction with toluene. Concentrated hydrochloric acid was added to the aqueous layer, and crystals precipitated were filtered, washed with water and dried to afford 7.1 g of 6-(4-ethoxycarbonyl-1-piperazinyl)nicotinic acid (yield 80%).

Workup

  1. temperatureAfter cooled crystals
  2. filtrationwere filtered, to the crystals
  3. additionwas added a solution of 2.6 g of sodium hydroxide in 30 ml of water
  4. extractionfollowed by extraction with toluene
  5. additionConcentrated hydrochloric acid was added to the aqueous layer, and crystals
  6. customprecipitated
  7. filtrationwere filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-c752dc77e3b44a7d98a3abd86b775d1c
Source dataset
uspto-grants-1991_06
Patent number
US05025012

Reaction notes

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