N-[4-(piperidine-4-carbonyl)-phenyl]methanesulfonamide hydrochloride → N-[4-[[1-[3-(4-Nitrophenoxy)propyl]-4-piperidinyl]carbonyl]phenyl]methanesulfonamide
Reaction equation
Cl.[CH3:2][S:3]([NH:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1)(=[O:5])=[O:4].[N+:21]([C:24]1[CH:34]=[CH:33][C:27]([O:28][CH2:29][CH2:30][CH2:31]I)=[CH:26][CH:25]=1)([O-:23])=[O:22]>>[N+:21]([C:24]1[CH:34]=[CH:33][C:27]([O:28][CH2:29][CH2:30][CH2:31][N:16]2[CH2:17][CH2:18][CH:13]([C:11]([C:10]3[CH:9]=[CH:8][C:7]([NH:6][S:3]([CH3:2])(=[O:4])=[O:5])=[CH:20][CH:19]=3)=[O:12])[CH2:14][CH2:15]2)=[CH:26][CH:25]=1)([O-:23])=[O:22]Participants
3
Procedure
4-(4-Methylsulfonylaminobenzoyl)piperidine hydrochloride (1.97 g, 6.19 mmol) and 1-(4-nitrophenoxy)-3-iodopropane (1.90 g, 6.19 mmol) were reacted by the procedure of Example 1 to afford 1.32 g (46%) of the desired product as a white solid: mp 162°-164° C.; 1H NMR (DMSO-d6): δ 10.29 (br s, 1H), 8.19 (d, J=9.30 Hz, 2H), 7.93 (d, J=8.86 Hz, 2H), 7.26 (d, J=8.84 Hz, 2H), 7.13 (d, J=9.31 Hz, 2H), 4.15 (t, J=6.34 Hz, 2H), 3.32 (m, 1H), 3.09 (s, 3H), 2.89 (m, 2H), 2.48 (m, 2H), 2.07 (m, 2H), 1.91 (m, 2H), 1.70 (m, 2H), 1.56 (m, 2H). IR (KBr): 3620, 3210, 2950, 1660, 1600 cm-1.
Sources & evidence
- ORD record
- ord-6d3ced95c3e949c78502467e8d9c18f5
- Source dataset
- uspto-grants-1993_10
- Patent number
- US05254689
Reaction notes
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