2-Pyrazinecarboxylic acid → N-(2-aminoethyl)pyrazine-2-carboxamide hydrochloride

HRID 34943Notes

Reaction equation

HRID 34943 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C(N(CC)CC)C.[CH2:17]([NH2:20])[CH2:18][NH2:19].C(Cl)[Cl:22]>ClC(OCC)=O>[ClH:22].[NH2:19][CH2:18][CH2:17][NH:20][C:7]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)=[O:9]

Participants

6

Reactant 4

HCID 10472-Pyrazinecarboxylic acidHCID 3301EthylenediamineHCID 6344Dichloromethane2×HCID 8471Triethylamine

Product 1

HCID 13800270N-(2-aminoethyl)pyrazine-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 10928Ethyl chloroformateSolvent

Procedure

A solution of 25.0 g of pyrazinecarboxylic acid in 300 ml of methylene chloride and 20.1 ml of ethyl chloroformate was treated dropwise at 0° within 1/2 hour with 31 ml of triethylamine. After 1/2 hour the solution obtained was added dropwise at 0° to 68 ml of ethylenediamine in 200 ml of methylene chloride and the mixture was left to stir further for 1 hour without external cooling. Thereafter, the precipitated material was filtered off and the filtrate was evaporated to dryness on a rotary evaporator under reduced pressure. The residue was recrystallized twice from isopropanol, whereby there was obtained N-(2-aminoethyl)pyrazine-2-carboxamide hydrochloride, m.p. 205°-207°.

Workup

  1. customAfter 1/2 hour the solution obtained
  2. waitthe mixture was left
  3. filtrationThereafter, the precipitated material was filtered off
  4. customthe filtrate was evaporated to dryness on a rotary evaporator under reduced pressure
  5. customThe residue was recrystallized twice from isopropanol

Sources & evidence

ORD record
ord-30ebef72dd23407daacc55c956298292
Source dataset
uspto-grants-1988_08
Patent number
US04764522

Reaction notes

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