Butylamine → N-Butyl-N-(1-phenyltetrazol-5-yl)amine

HRID 383149Notes

Reaction equation

HRID 383149 reaction equation
Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[N:4][N:3]=1.[CH2:13]([NH2:17])[CH2:14][CH2:15][CH3:16].C(N(C(C)C)CC)(C)C>CN(C=O)C.CCOC(C)=O>[CH2:13]([NH:17][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[N:4][N:3]=1)[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 8007ButylamineHCID 81531DiisopropylethylamineHCID 842621H-Tetrazole, 5-chloro-1-phenyl-

Product 1

HCID 12678651N-Butyl-N-(1-phenyltetrazol-5-yl)amineYield 52%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Chloro-1-phenyl-1H-tetrazole (1.00 g, 5.54 mmol), butylamine (0.547 mL, 5.54 mmol), and diisopropylethylamine (1.48 mL, 8.31 mmol) were dissolved in DMF (5 mL), and stirred overnight at room temperature. Reaction diluted with EtOAc and washed with water and brine. Organic layer dried with Na2SO4, filtered, and concentrated in vacuo. Residue purified by flash chromatography on silica gel eluting with 35% EtOAc/Hexanes to afford the desired product as a white solid (625 mg, 52%). m/e (DCI) 218 (MH+)

Workup

  1. customReaction
  2. washwashed with water and brine
  3. dry with materialOrganic layer dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customResidue purified by flash chromatography on silica gel eluting with 35% EtOAc/Hexanes

Sources & evidence

ORD record
ord-3fb3e22cae9a410c9661b109e2bc6d55
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

Loading…