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

HRID 1832216Notes

Reaction equation

HRID 1832216 reaction equation
C1(N2C3C(=CC=CC=3)C(CCCN3CCC(C4C=C(NC(=O)C(C)C)C=CC=4)CC3)=C2C2C=CC=CC=2)C=CC=CC=1.[CH3:43][CH:44]([CH3:73])[C:45]([NH:47][C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([CH:54]2[CH2:59][CH2:58][N:57]([CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][C:65](=O)[C:66]3[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=3)[CH2:56][CH2:55]2)[CH:49]=1)=[O:46].Cl.[CH3:75][O:76][C:77]1[CH:82]=[CH:81][C:80]([NH:83]N)=[CH:79][CH:78]=1>>[CH3:75][O:76][C:77]1[CH:82]=[C:81]2[C:80](=[CH:79][CH:78]=1)[NH:83][C:65]([C:66]1[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=1)=[C:64]2[CH2:63][CH2:62][CH2:61][CH2:60][N:57]1[CH2:58][CH2:59][CH:54]([C:50]2[CH:49]=[C:48]([NH:47][C:45](=[O:46])[CH:44]([CH3:43])[CH3:73])[CH:53]=[CH:52][CH:51]=2)[CH2:55][CH2:56]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 220488102-methyl-N-(3-[1-(6-oxo-6-phenylhexyl)-4-piperidinyl]phenyl}propanamide

Product 1

HCID 22048858N-(3-{1-[4-(5-methoxy-2-phenyl-1H-indol-3-yl)butyl]-4-piperidinyl}phenyl)-2-methylpropanamideYield 33%

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-(6-oxo-6-phenylhexyl)-4-piperidinyl]phenyl}propanamide (14.3 mg, 0.0339 mmol) and 1-(4-methoxyphenyl)hydrazine hydrochloride (7.10 mg, 0.0407 mmol) provided N-(3-{1-[4-(5-methoxy-2-phenyl-1H-indol-3-yl)butyl]-4-piperidinyl}phenyl)-2-methylpropanamide (5.8 mg, 33%). 1H NMR (400 MHz, CDCl3) δ 7.95 (d, 2H, J=7.8 Hz), 7.61–7.15 (m, 11H), 6.97 (d, 1H, J=7.0 Hz), 3.88 (s, 3H), 3.09 (d, 2H, J=11.3 Hz), 2.99 (t, 2H, J=7.0 Hz), 2.55–2.35 (m, 4H), 2.12–1.70 (m, 6H), 1.68–1.52 (m, 2H), 1.48–1.34 (m, 2H), 1.25 (d, 6H, J=6.7 Hz); ESMS m/e: 524.3 (M+H)+.

Sources & evidence

ORD record
ord-59604f3f014d43a28329e84095c3aab4
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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