Acetamide → 1-[2-(Dimethylamino)-1-(3-trifluoromethylphenoxy)ethyl]cyclohexanol

HRID 64745Notes

Reaction equation

C(N)(=O)C.FC(F)(F)[C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[O:10]CC(O)=O.[CH3:20][N:21]([CH3:36])[C:22](=O)[CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=1.B.O1CCCC1>>[CH3:20][N:21]([CH3:36])[CH2:22][CH:23]([C:9]1([OH:10])[CH2:15][CH2:16][CH2:17][CH2:7][CH2:8]1)[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=1

Participants

Reactant 4

HCID 178Acetamide

HCID 19914302-[3-(Trifluoromethyl)phenoxy]acetic acid

HCID 2723981Borane;tetrahydrofuran

HCID 13672711N,N-dimethyl-2-[3-(trifluoromethyl)phenoxy]acetamide

Product 1

HCID 136727071-[2-(Dimethylamino)-1-(3-trifluoromethylphenoxy)ethyl]cyclohexanol

Procedure

N,N-dimethyl-2-[3-trifluoromethyl)phenoxy]acetamide, prepared from 2-[3-trifluoromethylphenoxyl]acetic acid in accordance with Example 1 was converted to the amide which was reduced with Borane/tetrahydrofuran as in Example 3. The title compound was obtained and its hydrochloride salt prepared, m.p. 210°-211° C.

Sources & evidence

ORD record: ord-5586ff239db74521b6835527dab79dc2
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04609758

Reaction notes

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