Hydrazine, 1,1-diphenyl-, hydrochloride (1:1) → 2-methyl-N-(3-{1-[(1-phenyl-1H-indol-3-yl)methyl]-4-piperidinyl}phenyl)propanamide
Reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)C(CCCN3CCC(C4C=C(NC(=O)C(C)C)C=CC=4)CC3)=C2C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[CH:45](OC)[CH2:46][CH2:47][N:48]1[CH2:53][CH2:52][CH:51]([C:54]2[CH:55]=[C:56]([NH:60][C:61](=[O:65])[CH:62]([CH3:64])[CH3:63])[CH:57]=[CH:58][CH:59]=2)[CH2:50][CH2:49]1.Cl.C1(N(C2C=CC=CC=2)N)C=CC=CC=1>>[CH3:63][CH:62]([CH3:64])[C:61]([NH:60][C:56]1[CH:57]=[CH:58][CH:59]=[C:54]([CH:51]2[CH2:52][CH2:53][N:48]([CH2:47][C:46]3[C:2]4[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=4)[N:7]([C:15]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:45]=3)[CH2:49][CH2:50]2)[CH:55]=1)=[O:65]Participants
4
Reactant 3
Product 1
Procedure
According to the procedure used for the synthesis of N-(3-{1-[3-(1,2-diphenyl-1H-indol-3-yl)propyl]-4-piperidinyl}phenyl)-2-methylpropanamide, N-{3-[1-(3,3-dimethoxypropyl)-4-piperidinyl]phenyl}-2-methylpropanamide (15.2 mg, 0.0436 mmol) and 1,1-diphenylhydrazine hydrochloride (11.6 mg, 0.0524 mmol) provided 2-methyl-N-(3-{1-[(1-phenyl-1H-indol-3-yl)methyl]-4-piperidinyl}phenyl)propanamide (11 mg, 56%). 1H NMR (400 MHz, CDCl3) δ 7.79 (d, 1H, J=7.8 Hz), 7.57 (d, 1H, J=7.7 Hz), 7.54–7.47 (m, 4H), 7.43–7.32 (m, 4H), 7.25–7.16 (m, 4H), 6.95 (d, 1H, J=7.8 Hz), 3.87 (s, 2H), 2.53–2.47 (m, 2H), 2.21 (dt, 2H, J=3.0, 10.5 Hz), 2.12–1.77 (m, 6H), 1.24 (d, 6H, J=6.9 Hz); ESMS m/e: 451.3 (M+H)+.
Sources & evidence
- ORD record
- ord-adb28288a4c541c6b234d67e54b38e91
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07067534B1
Reaction notes
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