Dabco → HCID 15252135, compound

HRID 1534077Notes

Reaction equation

HRID 1534077 reaction equation
[O:1]([CH2:9][C:10]([F:13])([F:12])[F:11])[S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].[N:14]12[CH2:21][CH2:20][N:17]([CH2:18][CH2:19]1)[CH2:16][CH2:15]2>ClCCl>[O-:4][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:3])=[O:1].[F:11][C:10]([F:13])([F:12])[CH2:9][N+:14]12[CH2:21][CH2:20][N:17]([CH2:18][CH2:19]1)[CH2:16][CH2:15]2

Participants

4

Reactant 2

HCID 9237DabcoHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 15252135HCID 15252135, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2,2-Trifluoroethyl triflate (10.0 g, 43.1 mmol) was added slowly to a stirred, freshly-prepared solution of 1,4-diazabicyclo[2,2,2]octane (7.0 g, 62.5 mmol) in dichloromethane (50 cm3). The reaction mixture was stirred for 2 hours then filtered to remove a white precipitate, which was recrystallized from an ethanol-diethyl ether mixture to provide 1-(2,2,2-trifluoroethyl)-4-aza-1-azoniabicyclo [2,2,2]octane triflate (8.3 g, 24.1 mmol, 56%) (Found: C, 31.2; H, 3.8; N, 7.9%. Calc. C, 31.4; H, 4.1; N, 8.1%). m.p. 123°-125° C., δF (soln. in D2O; ext. CF3CO2H ref.) -0.2 (s; CF3SO3-) 17.8 (t, 3JHF 9 Hz; CF3CH2) p.p.m., δH (same solution) 3.30 (t; 3×ring CH2), 3.72 (t; 3×ring CH 2), 4.36 (q, 3JHF 9 Hz; CH2CF3) p.p.m.

Workup

  1. filtrationthen filtered
  2. customto remove a white precipitate, which
  3. customwas recrystallized from an ethanol-diethyl ether mixture

Sources & evidence

ORD record
ord-e99b29792c904a468f60ae9266a0f136
Source dataset
uspto-grants-1992_02
Patent number
US05086178

Reaction notes

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