N-(4-methylphenyl)indole → HCID 10162012, compound

HRID 2087201Notes

Reaction equation

HRID 2087201 reaction equation
Cl[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([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:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:30][C:31]1[CH:36]=[CH:35][C:34](N2C3C(=CC=CC=3)C=C2)=[CH:33][CH:32]=1>>[CH3:27][CH:26]([CH3:28])[C:25]([NH:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH:15]2[CH2:16][CH2:17][N:12]([CH2:11][C:6]3[C:5]4[C:9](=[CH:10][CH:2]=[CH:3][CH:4]=4)[N:8]([C:34]4[CH:35]=[CH:36][C:31]([CH3:30])=[CH:32][CH:33]=4)[CH:7]=3)[CH2:13][CH2:14]2)[CH:19]=1)=[O:29]

Participants

3

Reactant 2

HCID 9794286N-(4-methylphenyl)indoleHCID 10179729HCID 10179729, compound

Product 1

HCID 10162012HCID 10162012, compoundYield 78%

Procedure

According to the procedure used for the synthesis of N-(3-{1-[(6-chloro-1H-indol-3-yl)methyl]-4-piperidinyl}phenyl)-2-methylpropanamide, 1-(4-methylphenyl)-1H-indole (0.207 g, 1.00 mmol) provided 2-methyl-N-[3-(1-{[1-(4-methylphenyl)-1H-indol-3-yl]methyl}-4-piperidinyl)phenyl]propanamide (0.441 g, 78%). 1H NMR (400 MHz, CDCl3) δ 7.90 (s, 1H), 7.73 (d, 1H, J=7.2 Hz), 7.58-7.51 (m, 2H), 7.43-7.36 (m, 3H), 7.35-7.29 (m, 3H), 7.26-7.15 (m, 3H), 6.89 (d, 1H, J=7.7 Hz), 4.07 (s, 2H), 3.36 (d, 2H, J=11.6 Hz), 2.59-2.39 (m, 6H), 2.55 (sept, 1H, J=6.7 Hz), 2.10-1.98 (m, 2H), 1.83 (d, 2H, J=12.9 Hz), 1.23 (d, 6H, J=6.9 Hz); ESMS m/e: 466.2 (M+H)+.

Sources & evidence

ORD record
ord-dab2fa3a3b4d40fa89cbce90b09d9d1e
Source dataset
uspto-grants-2004_04
Patent number
US06727264B1

Reaction notes

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