Trifluoroacetic acid → 4-(4-(Heptyloxy)phenyl)piperidine
Reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2(O)[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]Participants
Procedure
To a stirring solution of tert-butyl 4-(4-(heptyloxy)phenyl)-4-hydroxypiperidine-1-carboxylate (388 mg, 0.99 mmol) and triethylsilane (791 μl, 4.95 mmol) in DCM (2 mL) cooled to −30° C. was slowly added 2,2,2-trifluoroacetic acid (379 μl, 4.95 mmol) in a drop-wise fashion. The reaction mixture was allowed to warm slowly and stirring continued for 16 h. The reaction mixture was poured onto ice-water/NaOH (50 mL/5 mL, 2 M) and extracted with DCM (3×20 mL). The combined organic extracts were washed successively with water (50 mL) and NaHCO3 (20 mL), dried over MgSO4 and evaporated to afford 166 mg (58%) of 4-(4-(heptyloxy)phenyl)piperidine INT-19 as a white, waxy solid. LCMS-ESI (m/z) calculated for C18H29NO: 275.4; found 276.0 [M+H]+, tR=2.88 min. (Method 11).
Workup
- temperatureto warm slowly
- additionThe reaction mixture was poured onto ice-water/NaOH (50 mL/5 mL, 2 M)
- extractionextracted with DCM (3×20 mL)
- washThe combined organic extracts were washed successively with water (50 mL) and NaHCO3 (20 mL)
- dry with materialdried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-4bc3d9021ed24138bcded300e4f886e9
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778923B2
Reaction notes
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