4-Methoxyphenylhydrazine hydrochloride → N-(3-{1-[3-(5-methoxy-2-phenyl-1H-indol-3-yl)propyl]-4-piperidinyl}phenyl)-2-methylpropanamide
Reaction equation
C1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[CH:26]=[C:27]([NH:31][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[CH:28]=[CH:29][CH:30]=4)[CH2:21][CH2:20]3)=[C:8]2[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)C=CC=CC=1.CC(C)[C:45](NC1C=CC=C(C2CCN(CCCCC(=O)C3C=CC=CC=3)CC2)C=1)=[O:46].Cl.COC1C=CC(NN)=CC=1>>[CH3:45][O:46][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[NH:7][C:8]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[C:9]2[CH2:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][CH:22]([C:25]2[CH:26]=[C:27]([NH:31][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[CH:28]=[CH:29][CH:30]=2)[CH2:23][CH2:24]1Participants
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, 2-methyl-N-{3-[1-(5-oxo-5-phenylpentyl)-4-piperidinyl]phenyl}propanamide (15.6 mg, 38.2 mmol), and 1-(4-methoxyphenyl)hydrazine hydrochloride (8.00 mg, 0.0458 mmol) provided N-(3-{1-[3-(5-methoxy-2-phenyl-1H-indol-3-yl)propyl]-4-piperidinyl}phenyl)-2-methylpropanamide (3.9 mg, 20%). 1H NMR (400 MHz, CDCl3) δ 8.06 (s, 1H), 7.55 (d, 2H, J=7.4 Hz), 7.43–7.39 (m, 3H), 7.38–7.35 (m, 2H), 7.27–7.19 (m, 3H), 7.08 (d, 1H, J=7.4 Hz), 6.94 (d, 1H, J=7.6 Hz), 6.87 (dd, 1H, J=4.0, 6.6 Hz), 3.88 (s, 3H), 3.80–3.69 (m, 1H), 2.99 (d, 2H, J=11.7 Hz), 2.89 (t, 2H, J=7.3), 2.55–2.39 (m, 4H), 2.02–1.88 (m, 3H), 1.82–1.68 (m, 4H), 1.24 (d, 6H, J=6.9 Hz); ESMS m/e: 510.3 (M+H)+.
Sources & evidence
- ORD record
- ord-69e1396c2ed346c5a28f92e08ee38d2e
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07067534B1
Reaction notes
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