Sodium cyanoborohydride → HCID 19862545, compound

HRID 1165156Notes

Reaction equation

HRID 1165156 reaction equation
[OH:1][C:2]1[C:20]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:19][C:5]([CH:6]=[N:7][N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:4][C:3]=1[C:25]([CH3:28])([CH3:27])[CH3:26].C([BH3-])#N.[Na+]>C(O)(=O)C>[OH:1][C:2]1[C:20]([C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:19][C:5]([CH2:6][NH:7][N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:4][C:3]=1[C:25]([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 136209504HCID 136209504, compound

Product 1

HCID 19862545HCID 19862545, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.92 g of 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)-2-morpholinoimidazole are dissolved in 30 ml of glacial acetic acid and treated portionwise within 30 minutes with 0.7 g of 90% sodium cyanoborohydride. The reaction mixture is stirred overnight. The solvent is removed by evaporation in a vacuum and the residue is treated with 20 ml of water. Saturated sodium carbonate solution is added up to an alkaline reaction and the mixture is extracted three times with 20 ml of methylene chloride each time. The organic phases are combined, dried over sodium sulfate, filtered and evaporated. The residue is boiled up briefly with 20 ml of n-hexane. After cooling, the crystalline colorless product is removed by filtration and recrystallized from methanol/water. There is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylamino)-2-morpholinoimidazole of m.p. 161°-163°.

Workup

  1. customThe solvent is removed by evaporation in a vacuum
  2. additionthe residue is treated with 20 ml of water
  3. additionSaturated sodium carbonate solution is added up to an alkaline reaction
  4. extractionthe mixture is extracted three times with 20 ml of methylene chloride each time
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. temperatureAfter cooling
  9. customthe crystalline colorless product is removed by filtration
  10. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-73aee451e4c14e67a9853a9be6da5ece
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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