Hydrochloric Acid → HCID 178440810, compound

HRID 534919Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:21])[CH2:18][C:19]#[N:20])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[N-:22]=[N+:23]=[N-:24].[Na+].Cl>O.[Br-].[Zn+2].[Br-]>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17](=[O:21])[CH2:18][C:19]2[NH:24][N:23]=[N:22][N:20]=2)[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 150 °C

Procedure

A stirred suspension of 3-(4-(2-tert-butylphenyl)piperazin-1-yl)-3-oxopropanenitrile (0.060 g, 0.21 mmol), sodium azide (0.015 g, 0.23 mmol) and zinc bromide (0.055 g, 0.21 mmol) in water (1.0 mL) was heated at 150° C. for 24 h. After this time, the reaction mixture was cooled to room temperature, acidified with 1.0 M hydrochloric acid to pH 1-2 and extracted with ethyl acetate (3×15 mL). The combined organics were washed with water, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was triturated with acetonitrile to provide 1-(4-(2-tert-butylphenyl)piperazin-1-yl)-2-(1H-tetrazol-5-yl)ethanone (0.018 g, 27%) as an off-white solid, mp 236-237° C.

Workup

temperatureAfter this time, the reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate (3×15 mL)
washThe combined organics were washed with water
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was triturated with acetonitrile

Sources & evidence

ORD record: ord-8f4cb3c599a148fd9a7ad27f2c0c0fc1
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853215B2

Reaction notes

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