4-Methoxyphenylhydrazine hydrochloride → N-(3-{1-[3-(5-methoxy-1H-indol-3-yl)propyl]-4-piperidinyl}phenyl)-2-methylpropanamide

HRID 1832219Notes

Reaction equation

HRID 1832219 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]2C2C=CC=CC=2)C=CC=CC=1.[O:43]1CCO[CH:44]1CCCCN1CCC(C2C=C(NC(=O)C(C)C)C=CC=2)CC1.Cl.COC1C=CC(NN)=CC=1>>[CH3:44][O:43][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[NH:7][CH:8]=[C:9]2[CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:26]=[C:27]([NH:31][C:32](=[O:36])[CH:33]([CH3:34])[CH3:35])[CH:28]=[CH:29][CH:30]=2)[CH2:21][CH2:20]1

Participants

4

Reactant 3

HCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 10209625N-(3-(1-[3-(1,2-diphenyl-1H-indol-3-yl)propyl]-4-piperidinyl}phenyl)-2-methylpropanamideHCID 22048802N-(3-{1-[4-(1,3-dioxolan-2-yl)butyl]4-piperidinyl}phenyl)-2-methylpropanamide

Product 1

HCID 10181321N-(3-{1-[3-(5-methoxy-1H-indol-3-yl)propyl]-4-piperidinyl}phenyl)-2-methylpropanamideYield 42%

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-[4-(1,3-dioxolan-2-yl)butyl]-4-piperidinyl}phenyl)-2-methylpropanamide (23.5 mg, 0.0628 mmol) and 1-(4-methoxyphenyl)hydrazine hydrochloride (13.2 mg, 0.0774 mmol) provided N-(3-{1-[3-(5-methoxy-1H-indol-3-yl)propyl]-4-piperidinyl}phenyl)-2-methylpropanamide (11 mg, 42%). 1H NMR (400 MHz, CDCl3) δ 7.86 (s, 1H), 7.45 (s, 1H), 7.32 (d, 1H, J=8.4 Hz), 7.28–7.21 (m, 2H), 7.10 (s, 1H), 7.05 (d, 1H, J=2.3 Hz), 7.00–6.91 (m, 2H), 6.85 (dd, 1H, J=2.7, 9.0 Hz), 3.87 (s, 3H), 3.06 (d, 2H, J=11.6 Hz), 2.75 (t, 2H, J=7.2 Hz), 2.55–2.42 (m, 4H), 2.08–1.90 (m, 4H), 1.88–1.74 (m, 49), 1.25 (d, 6H, J=6.9 Hz); ESMS m/e: 434.2 (M+H)+.

Sources & evidence

ORD record
ord-61ef66af926f4a169fffd09881b87621
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

Loading…