Trifluoroacetic acid → 4-[4-[2-(N-Dodecyl-N-propylamino]ethoxy]phenyl]-1,1,1-trifluoro-2-butanone

HRID 1700916Notes

Reaction equation

HRID 1700916 reaction equation
[CH2:1]([N:4]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](OC)([O:21]C)[C:17]([F:20])([F:19])[F:18])=[CH:10][CH:9]=1)[CH2:2][CH3:3].FC(F)(F)C(O)=O.C(N(CCCC(OCC)=O)CCOC1C=CC(CCC(=O)C(F)(F)F)=CC=1)CCCCCCCCCCC>>[CH2:25]([N:4]([CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16](=[O:21])[C:17]([F:19])([F:20])[F:18])=[CH:12][CH:13]=1)[CH2:1][CH2:2][CH3:3])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 18319117N-Propyl-N-[2-[4-(4,4,4-trifluoro-3,3-dimethoxybut-1-yl)phenoxy]ethyl]dodecylamineHCID 867571224-[N-dodecyl-N-[2-[4-(3oxo-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]amino]butanoic acid, ethyl ester

Product 1

HCID 183190544-[4-[2-(N-Dodecyl-N-propylamino]ethoxy]phenyl]-1,1,1-trifluoro-2-butanoneYield 62%

Procedure

N-Propyl-N-[2-[4-(4,4,4-trifluoro-3,3-dimethoxybut-1-yl)phenoxy]ethyl]dodecylamine (300 mg, 0.58 mmol) was treated with trifluoroacetic acid as described in the preparation of 4-[N-dodecyl-N-[2-[4-(4,4,4-trifluoro-3-oxobut-1-yl)phenoxy]ethyl]amino]butanoic acid, ethyl ester and afforded the title compound (169 mg, 62%) as a pale yellow oil.

Sources & evidence

ORD record
ord-c257d03876b2414684182cf97b065af7
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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