1-(4-Fluorophenyl)-4-(methylsulfonyl)piperazine → 1-{[(1E)-3,3-dimethyloct-1-en-5-yn-1-yl]sulfonyl}-4-(4-fluoro phenyl)piperazine
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:18][C:19]([CH3:27])([CH2:22][C:23]#[C:24][CH2:25][CH3:26])[CH:20]=O>>[CH3:18][C:19]([CH3:27])([CH2:22][C:23]#[C:24][CH2:25][CH3:26])/[CH:20]=[CH:17]/[S:14]([N:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10]1)(=[O:15])=[O:16]Participants
3
Procedure
The title compound was prepared, following procedure described in Example 1, step a), but starting from 1-(4-fluorophenyl)-4-(methylsulfonyl)piperazine (Intermediate B1, 855 mg; 3.31 mmol) and of 2,2-dimethyl-hept-4-ynal, 457 mg; 3.31 mmol), as a white powder (764 mg, 61% yield). HPLC, Rt: 4.75 min (purity: 97.7%). LC/MS, M+(ESI): 379.4, 1H NMR (DMSO-d6) δ: 6.97-6.82 (m, 4H), 6.74 (d, J=15.4 Hz, 1H), 6.07 (d, J=14.9 Hz, 3.26 (m, 4H), 3.15 (m, 4H), 2.21 (m, 2H), 2.01-2.16 (m, 2H), 1.15 (s, 6H), 1.06 (t, J=7.4 Hz, 3H).
Sources & evidence
- ORD record
- ord-3142209b436d44809bfa3411d8295263
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973039B2
Reaction notes
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