Water → HCID 67229211, compound

HRID 1896181Notes

Reaction equation

HRID 1896181 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[CH2:12]([NH:19][CH2:20][CH2:21][NH2:22])[C:13]1C=CC=CC=1.[OH2:23]>>[ClH:1].[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([N:22]2[CH2:21][CH2:20][NH:19][CH2:12][C:13]2=[O:23])=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 962WaterHCID 77801N-BenzylethylenediamineHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 67229211HCID 67229211, compound

Procedure

10 g of 2-chloro-5-(trifluoromethyl)pyridine and 40.5 ml of N-benzylethylenediamine are heated at 135° C. for 6 hours in a round-bottomed flask. The resulting mixture is poured into water and extracted with ethyl acetate. The extracts are dried and evaporated under vacuum; the crude product thus obtained is purified by flash chromatography. The isolated product (compound of formula (VIII)), 14 g, is dissolved in 200 ml of 2N HCl solution. 30 g of trimeric glyoxal dihydrate are added and the mixture is stirred at room temperature for 72 hours. The resulting mixture is extracted with ethyl acetate. The extracts are dried and evaporated under vacuum; the crude product thus obtained is purified by flash chromatography. The isolated product, 10 g, is dissolved in 450 ml of ethanol, followed by addition of 15 ml of a solution of isopropanol saturated with HCl and 3 g of 10% Pd/C. This mixture is reacted under a stream of hydrogen for 4 hours at a temperature of 40° C. The resulting mixture is filtered and evaporated under vacuum to give 3 g of the title compound, m.p.=205-207° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extracts are dried
  3. customevaporated under vacuum
  4. customthe crude product thus obtained
  5. customis purified by flash chromatography
  6. dissolutionThe isolated product (compound of formula (VIII)), 14 g, is dissolved in 200 ml of 2N HCl solution
  7. addition30 g of trimeric glyoxal dihydrate are added
  8. extractionThe resulting mixture is extracted with ethyl acetate
  9. customThe extracts are dried
  10. customevaporated under vacuum
  11. customthe crude product thus obtained
  12. customis purified by flash chromatography
  13. dissolutionThe isolated product, 10 g, is dissolved in 450 ml of ethanol
  14. additionfollowed by addition of 15 ml of a solution of isopropanol saturated with HCl and 3 g of 10% Pd/C
  15. customThis mixture is reacted under a stream of hydrogen for 4 hours at a temperature of 40° C
  16. filtrationThe resulting mixture is filtered
  17. customevaporated under vacuum

Sources & evidence

ORD record
ord-b235b20fe6984077baef7c4dba1f947c
Source dataset
uspto-grants-2013_08
Patent number
US08518947B2

Reaction notes

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