Hydrochloric Acid → 1-(4-Chloro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7), 3,5-trien-10-yl)-2,2,2-trifluoro-ethanone

HRID 10097

Reaction equation

N[C:2]1[CH:12]=[CH:11][C:10]2[CH:9]3[CH2:13][CH:5]([CH2:6][N:7]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH2:8]3)[C:4]=2[CH:3]=1.N([O-])=O.[Na+].[ClH:24]>O.Cl[Cu]>[Cl:24][C:2]1[CH:12]=[CH:11][C:10]2[CH:9]3[CH2:13][CH:5]([CH2:6][N:7]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH2:8]3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1-(4-Amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (460 mg, 1.7 mmol) was dissolved in H2O (2 mL) and concentrated HCl solution(1 mL) then cooled to 0° C. and treated with a solution of sodium nitrite (NaNO2) (275 mg) in H2O (1 mL) dropwise. To the resulting solution was added a CuCl (202 mg, prepared as described above, 2.04 mmol) in concentrated HCl solution (2 mL) over 10 minutes (gas evolution observed). The resulting solution was warmed to 60° C. for 15 minutes, then was cooled to room temperature and extracted with ethyl acetate (4×30 mL). After drying over Na2SO4, the solution was filtered and concentrated to an oil which was filtered through a Silica pad to remove baseline material eluting with 50% ethyl acetate/hexanes to give an oil (470 mg, 95%).

Workup

temperaturewas cooled to room temperature
extractionextracted with ethyl acetate (4×30 mL)
dry with materialAfter drying over Na2SO4
filtrationthe solution was filtered
concentrationconcentrated to an oil which
filtrationwas filtered through a Silica pad
customto remove baseline material
washeluting with 50% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-a0e1cb1ebb244b41a71131589d967acf
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091372B2

Linked notes

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