5-[[3-[3-[(Dimethylamino)methyl]phenoxy]propyl]amino]-1-methyl-1H-1,2,4-triazole-3-carbamic acid, ethyl ester → HCID 54282945, compound

HRID 2058730Notes

Reaction equation

HRID 2058730 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][CH:27]=1)[O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[N:17]([CH3:18])[N:16]=[C:15]([NH:19][C:20](OCC)=O)[N:14]=1)[CH3:3]>O1CCCC1>[CH3:18][N:17]1[C:13]([NH:12][CH2:11][CH2:10][CH2:9][O:8][C:7]2[CH:25]=[CH:26][CH:27]=[C:5]([CH2:4][N:2]([CH3:3])[CH3:1])[CH:6]=2)=[N:14][C:15]([NH:19][CH3:20])=[N:16]1

Participants

3

Reactant 1

HCID 540960345-[[3-[3-[(Dimethylamino)methyl]phenoxy]propyl]amino]-1-methyl-1H-1,2,4-triazole-3-carbamic acid, ethyl ester

Product 1

HCID 54282945HCID 54282945, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[[3-[3-[(dimethylamino)methyl]phenoxy]propyl]amino]-1-methyl-1H-1,2,4-triazole-3-carbamic acid, ethyl ester (0.35 g) lithium aluminum hydride (0.13 g) and tetrahydrofuran (10 ml) was heated under reflux for 48 h. The mixture was quenched with water (0.5 ml), filtered and the filtrate was evaporated. The residue was purified by column chromatography on silica with methanol as the eluant to give the title compound as a pale yellow oil (0.1 g). TLC silica; methanol/0.88 ammonia 80:1, Rf 0.43. NMR (CDCl3) 2.78 t (1H); 3.0-3.3 m (3H); 5.47 t (1H); 5.95 t+brs (3H); 6.50 q (2H); 6.6 s (5H); 7.17 t (3H); 7.78 s (6H); 7.93 m (2H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 h
  3. customThe mixture was quenched with water (0.5 ml)
  4. filtrationfiltered
  5. customthe filtrate was evaporated
  6. customThe residue was purified by column chromatography on silica with methanol as the eluant

Sources & evidence

ORD record
ord-55518fb546864a8c981e13519c917703
Source dataset
uspto-grants-1982_03
Patent number
US04318913

Reaction notes

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