Sodium Iodide → N-(3-{1-[6-(1H-Indol-1-YL)hexyl]-4-piperidinyl}phenyl)-2-methylpropanamide

HRID 1832270Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1.[CH3:17][CH:18]([CH3:34])[C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:23]=1)=[O:20].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C>[N:8]1([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:31]2[CH2:32][CH2:33][CH:28]([C:24]3[CH:23]=[C:22]([NH:21][C:19](=[O:20])[CH:18]([CH3:17])[CH3:34])[CH:27]=[CH:26][CH:25]=3)[CH2:29][CH2:30]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(6-Chlorohexyl)-1H-indole (23.6 mg, 0.100 mmol), 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide (24.6 mg, 0.100 mmol), K2CO3 (27.6 mg, 0.200 mmol), NaI (22.5 mg, 0.150 mmol) and DMF (1.00 mL) was heated at 100° C. for 12 h. The reaction mixture was cooled to room temperature and the crude material was purified by preparative TLC using 5% of NH3 (2.0 M in methanol) in CH2Cl2 to give the desired product as a yellow solid (40 mg, 90%): 1H NMR (400 MHz, CDCl3) δ 8.08–6.52 (m, 11H), 4.17 (t, 2H, J=7.2 Hz), 3.26 (d, 2H, J=11.6 Hz), 2.74–2.52 (m, 4H), 2.44–2.28 (m, 2H), 2.20–2.02 (m, 2H), 1.98–1.82 (m, 4H) 1.78–1.62 (m, 2H), 1.43–1.28 (m, 4H), 1.28 (d, 6H, J=6.8 Hz); ESMS m/e: 446.5 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe crude material was purified by preparative TLC

Sources & evidence

ORD record: ord-d9c2643351cf4a37bbdc74a76d116b00
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067534B1

Reaction notes

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