Benzylamine → HCID 178520063, compound

HRID 485396Notes

Reaction equation

HRID 485396 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[O:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]1[N:15](C)[N:14]=[C:13]([CH2:17][OH:18])[N:12]=1)=O.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[BH4-].[Na+]>C(O)C>[C:23]1([CH2:22][NH:29][CH2:1][C:3]2[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=2)[O:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]2[NH:15][N:14]=[C:13]([CH2:17][OH:18])[N:12]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 4311764Sodium borohydrideHCID 20270297HCID 20270297, compound

Product 1

HCID 178520063HCID 178520063, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-[[3-(3-formylphenoxy)propyl]amino]-1-methyl-1H-1,2,4-triazole-3-methanol (532 mg) in ethanol (15 ml) was treated with benzylamine (5 ml) and stirred at room temperature for 1.5 h. The solution was treated with sodium borohydride (500 mg) and stirred at room temperature for 16 h. The mixture was evaporated, and the residue partitioned between 2N hydrochloric acid and ethyl acetate. The aqueous layer was washed with ethyl acetate, neutralised with potassium carbonate, and extracted with ethyl acetate. The combined extracts were dried and evaporated in vacuo to yield an oil. This oil was chromatographed on silica gel, using a mixture of methanol-ethyl acetate (1:1) to give the title compound as an oil (315 mg).

Workup

  1. stirringstirred at room temperature for 16 h
  2. customThe mixture was evaporated
  3. customthe residue partitioned between 2N hydrochloric acid and ethyl acetate
  4. washThe aqueous layer was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. customThe combined extracts were dried
  7. customevaporated in vacuo
  8. customto yield an oil
  9. customThis oil was chromatographed on silica gel
  10. additiona mixture of methanol-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-517518395ae64c3eabc0ca40b65987f5
Source dataset
uspto-grants-1985_08
Patent number
US04536508

Reaction notes

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