Dabco → HCID 15252136, compound

HRID 1534075Notes

Reaction equation

[O:1]([CH2:9][CH3:10])[S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].[N:11]12[CH2:18][CH2:17][N:14]([CH2:15][CH2:16]1)[CH2:13][CH2:12]2>C(#N)C>[O-:4][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:3])=[O:1].[CH2:18]([N+:11]12[CH2:10][CH2:9][N:14]([CH2:15][CH2:16]1)[CH2:13][CH2:12]2)[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl triflate (3.56 g, 20.0 mmol) was added dropwise to a cold (0° C.) stirred solution of 1,4-diazabicyclo[2,2,2]octane (3.26 g, 29.1 mmol) in dry acetonitrile (25 cm3) under dry nitrogen. The reaction mixture was stirred at 0° C. for 1 hour and then at 20° C. for 3 hours; no precipitate appeared. The solution was rotary evaporated at water-pump pressure, and the white solid residue remaining was washed with cold diethyl ether to remove unreacted 1,4-diazabicyclo-[2,2,2]octane and then dried in vacuo, to give 1-ethyl-4-aza-1-azoniabicyclo[2,2,2]octane triflate (5.30 g, 18.3 mmol, 91.5%) shown by 1H n.m.r. analysis to contain a trace of 1,4-diethyl-1,4-diazoniabicyclo[2,2,2]octane ditriflate. A pure sample of the monoquaternary salt, m.p. 117°-119° C., δH (D2O soln.) 1.32 (tt; N+CH2CH), 3.18 (m; 3×ring CH2), 3.25-3.4 (complex, two overlapping absorption systems; 3×ring CH2 +N+CH2CH3), p.p.m., δF (same soln.; ext. CF3CO2H ref.) 0.03 (s; CF3SO3-) p.p.m., was obtained by recrystallizing the slightly impure product from an ethanol-diethyl ether mixture.

Workup

waitat 20° C. for 3 hours
customThe solution was rotary evaporated at water-pump pressure
washthe white solid residue remaining was washed with cold diethyl ether
customto remove unreacted 1,4-diazabicyclo-[2,2,2]octane
customdried in vacuo

Sources & evidence

ORD record: ord-d397b0794cd449e183a2ce451cbf6e45
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05086178

Reaction notes

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