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

HRID 325708Notes

Reaction equation

HRID 325708 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 aluminium 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-c7bfe69f0c49401fba1e93ca22967bec
Source dataset
uspto-grants-1984_04
Patent number
US04442110

Reaction notes

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