Sodium borohydride → HCID 15586345, compound

HRID 2290329Notes

Reaction equation

HRID 2290329 reaction equation
[BH4-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:13]=[N:14][C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:16]([CH3:18])[N:17]=2)[CH2:8][CH2:7]1>CO>[OH:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[NH:13][N:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:16]([CH3:18])[N:17]=2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20232096HCID 20232096, compound

Product 1

HCID 15586345HCID 15586345, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (2.72 g) was added portionwise to a stirred solution of 3-[4-(2-hydroxyethyl)-1-piperazinyl]-5-methyl-6-phenyl-1,2,4-triazine (3.6 g) in methanol (15 ml) at room temperature. The reaction mixture was filtered by suction and the filtrate was evaporated. The resultant residue was extracted with ethyl acetate after addition of water, and the extract was washed with brine, dried over sodium sulfate and concentrated to a small volume. The resultant precipitates were collected by filtration, washed with diisopropyl ether and recrystallized from a mixture of ethyl acetate and diisopropyl ether to give 3-[4-(2-hydroxyethyl)-1-piperazinyl]-5-methyl-6-phenyl-2,5-dihydro-1,2,4-triazine (2.28 g), mp 103°~105° C.

Workup

  1. filtrationThe reaction mixture was filtered by suction
  2. customthe filtrate was evaporated
  3. extractionThe resultant residue was extracted with ethyl acetate
  4. additionafter addition of water
  5. washthe extract was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to a small volume
  8. customThe resultant precipitates
  9. filtrationwere collected by filtration
  10. washwashed with diisopropyl ether
  11. customrecrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-4a34799215e246a4b9d086de239470a2
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

Loading…