Potassium Hydroxide → 4-(3-Cyclopentylpropyl)-1-Phenyl-5-Tetrazolone

HRID 863802Notes

Reaction equation

[C:1]1([N:7]2[C:11](=[O:12])[N:10]=[N:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[CH:15]1([CH2:20][CH2:21][CH2:22]I)[CH2:19][CH2:18][CH2:17][CH2:16]1>CN(C)C=O>[CH:15]1([CH2:20][CH2:21][CH2:22][N:10]2[C:11](=[O:12])[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[N:9]2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 600 mg of 1-phenyl-5-tetrazolone (for the synthesis of this compound see: Horwitz, J. P.; Fisher, B. E.; Tomasewski, A. J. J Amer Chem Soc 1959, 81, 3076) in 2 mL of N,N-dimethylformamide (DMF) was added 280 mg of powdered 85% potassium hydroxide followed by 870 mg of 3-cyclopentyl-1-iodopropane from Step A. The mixture was stirred at 80° C. for 18 h and then quenched by addition of water. The product was extracted with dichloromethane and purification by flash chromatography on silica gel (9:1 hexane:ethyl acetate) afforded 830 mg of the title compound: 1H NMR (CDCl3) δ7.96 (d, 2H, J=8.5 Hz), 7.50 (t, 2H, J=7.5 Hz), 7.37 (t, 1H, J=7.5 Hz), 4.02 (t, 2H, J=7.1 Hz), 1.90 (m, 3H), 1.79 (m, 2H), 1.61 (m, 2H), 1.53 (m, 2H), 1.41 (m, 2H), 1.10 (m, 2H).

Workup

customquenched by addition of water
extractionThe product was extracted with dichloromethane and purification by flash chromatography on silica gel (9:1 hexane:ethyl acetate)

Sources & evidence

ORD record: ord-c94425c2ac5c44f0bdc5ae7bbf2a27d4
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05561142

Reaction notes

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