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

HRID 1700918Notes

Reaction equation

HRID 1700918 reaction equation
[CH2:1]([N:7]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19](OC)([O:24]C)[C:20]([F:23])([F:22])[F:21])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].FC(F)(F)C(O)=O.C(N(CCCC(OCC)=O)CCOC1C=CC(CCC(=O)C(F)(F)F)=CC=1)CCCCCCCCCCC>>[CH2:28]([N:7]([CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][C:19](=[O:24])[C:20]([F:22])([F:23])[F:21])=[CH:15][CH:16]=1)[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 18319019N-Hexyl-N-[2-[4-(3,3-dimethoxy-4,4,4-trifluorobut-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 183190214-[4-[2-(N-Dodecyl-N-Hexylamino]ethoxy]phenyl]-1,1,1-trifluoro-2-butanoneYield 78.2%

Procedure

N-Hexyl-N-[2-[4-(3,3-dimethoxy-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]dodecylamine (353 mg, 0.63 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 . The residue was chromatographed on silica gel (dichloromethane/methanol 98:2 to 94:6) to afford the title compound (253 mg, 78%) as a pale yellow oil.

Workup

  1. customThe residue was chromatographed on silica gel (dichloromethane/methanol 98:2 to 94:6)

Sources & evidence

ORD record
ord-8903069240954f22bf2ea5c367c34aee
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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