Aluminium lithium hydride → HCID 178520062, compound

HRID 485387Notes

Reaction equation

HRID 485387 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:27]=[CH:28][CH:29]=2)[O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]2[NH:21][N:20]=[C:19]([C:22](OCC)=[O:23])[N:18]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:27]=[CH:28][CH:29]=2)[O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]2[NH:21][N:20]=[C:19]([CH2:22][OH:23])[N:18]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178470502HCID 178470502, compound

Product 1

HCID 178520062HCID 178520062, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 5-[4-[3-(1-piperidinylmethyl)phenoxy]butyl]amino-1H-1,2,4-triazole-3-carboxylate (0.3 g) and lithium aluminium hydride (0.1 g) in tetrahydrofuran (50 ml) was stirred at room temperature for 0.5 h, then quenched with water. The solid was filtered off and washed with methanol. The filtrate and washings were evaporated to leave a residue which was extracted with hot ethyl acetate. Evaporation of the extract gave an oil that solidified. It was crystallised from ethyl acetate to give the title compound as an off-white solid (0.094 g) m.p. 127°-8° dec. tlc System B, Rf 0.7.

Workup

  1. customquenched with water
  2. filtrationThe solid was filtered off
  3. washwashed with methanol
  4. customThe filtrate and washings were evaporated
  5. customto leave a residue which
  6. extractionwas extracted with hot ethyl acetate
  7. customEvaporation of the extract
  8. customgave an oil that solidified
  9. customIt was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-5a4cdd09b9684c69901184de353d2b25
Source dataset
uspto-grants-1985_08
Patent number
US04536508

Reaction notes

Loading…