Hydrogen Bromide → HCID 13686022, compound

HRID 1380523Notes

Reaction equation

HRID 1380523 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:31]=[C:20]3[N:21]=[CH:22][CH:23]=[C:24]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[N:19]3[N:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.Br>CCOCC>[N:14]1([C:17]2[N:31]=[C:20]3[N:21]=[CH:22][CH:23]=[C:24]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[N:19]3[N:18]=2)[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 13686000HCID 13686000, compound

Product 1

HCID 13686022HCID 13686022, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an 8.0 g amount of 4-[7-(4-pyridyl)[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-1-piperazine carboxylic acid benzyl ester in 125 ml round bottom flask was added 25.0 ml of hydrobromic acid (31% in glacial acetic acid). The mixture was allowed to react for 20 minutes then was cooled. Ether was added to separate the precipitate. The precipitate was collected by filtration and dissolved in water. The solution was adjusted to a pH greater than pH 7 with 5N sodium hydroxide and extracted with three equal portions of chloroform. The extracts were combined and evaporated in vacuo to a syrup. The syrup was dissolved in hot ethanol and hexane was added to crystallize the crude product which was collected and washed with hexane. The crude product was recrystallized from 25 ml of cold ethanol, filtered, washed with ethanol/hexane then hexane. The material was dried in vacuo at 60° C. and gave 4.2 g of the product of the example as yellow crystals, mp 147°- 149° C.

Workup

  1. customto react for 20 minutes
  2. temperaturethen was cooled
  3. customto separate the precipitate
  4. filtrationThe precipitate was collected by filtration
  5. dissolutiondissolved in water
  6. extractionextracted with three equal portions of chloroform
  7. customevaporated in vacuo to a syrup
  8. dissolutionThe syrup was dissolved in hot ethanol
  9. additionhexane was added
  10. customto crystallize the crude product which
  11. customwas collected
  12. washwashed with hexane
  13. customThe crude product was recrystallized from 25 ml of cold ethanol
  14. filtrationfiltered
  15. washwashed with ethanol/hexane
  16. customThe material was dried in vacuo at 60° C.

Sources & evidence

ORD record
ord-7a9637e318b5421287e7a31ed319f7bb
Source dataset
uspto-grants-1986_04
Patent number
US04582833

Reaction notes

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