Reaction equation
ClC1C=CC(O[C:7]2[CH:31]=[CH:30][C:10]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([C:18]4[CH:19]=[C:20]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[CH:21]=[CH:22][CH:23]=4)[CH2:14][CH2:13]3)=[CH:9][CH:8]=2)=CC=1.[CH2:34]([N:36]1C2C=CC(CN3CCC(C4C=CC(NC(=O)C(C)C)=CC=4)CC3)=CC=2[C:42]2[C:37]1=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH3:35].C(N1C2C=CC(C=O)=CC=2C2C1=CC=CC=2)C.CC(C)C(NC1C=CC=C(C2CCNCC2)C=1)=O>>[CH2:34]([N:36]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([C:18]4[CH:19]=[C:20]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[CH:21]=[CH:22][CH:23]=4)[CH2:14][CH2:13]3)=[CH:30][C:31]=2[C:42]2[C:37]1=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH3:35]Participants
5
Reactant 4
Product 1
Procedure
According to the procedure used for the synthesis of N-(3-{1-[4-(4-CHLOROPHENOXY)BENZYL]-4-PIPERIDINYL}PHENYL)-2-METHYLPROPANAMIDE (Example 108) N-(4-{1-[(9-ethyl-9H-carbazol-3-yl)methyl]-4-piperidinyl}phenyl)-2-methylpropanamide, 9-ethyl-9H-carbazole-3-carbaldehyde and 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide afforded N-(3-{1-[(9-ethyl-9H-carbazol-3-yl)methyl]-4-piperidinyl}phenyl)-2-methylpropanamide (37 mg, 95%). 1H NMR (400 MHz, CDCl3) δ 8.24-6.29 (m, 12H), 4.37 (q, 2H, J=7.2 Hz), 3.82 (s, 2H), 3.23-3.06 (m, 2H), 2.65-2.38 (m, 2H), 2.31-2.11 (m, 2H), 2.01-1.73 (m, 4H), 1.43 (t, 3H, J=7.2 Hz), 1.25 (d, 6H, J=4.0 Hz); ESMS m/e: 454.3 (M+H)+.
Sources & evidence
- ORD record
- ord-ff6cc0dc016b4568a934942d0d055c75
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06727264B1
Linked notes
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