Sodium Iodide → N-(3-{1-[5-(1H-Indol-1-YL)pentyl]-4-piperidinyl}phenyl)-2-methylpropanamide

HRID 1832227Notes

Reaction equation

HRID 1832227 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.[CH3:16][CH:17]([CH3:33])[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:22]=1)=[O:19].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C>[N:7]1([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:30]2[CH2:31][CH2:32][CH:27]([C:23]3[CH:22]=[C:21]([NH:20][C:18](=[O:19])[CH:17]([CH3:16])[CH3:33])[CH:26]=[CH:25][CH:24]=3)[CH2:28][CH2:29]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 123407581-(5-Chloropentyl)-1H-indoleHCID 167572552-methyl-N-[3-(4-piperidyl)phenyl]propanamide

Product 1

HCID 22049385N-(3-{1-[5-(1H-Indol-1-YL)pentyl]-4-piperidinyl}phenyl)-2-methylpropanamideYield 83.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared as above, using 1-(5-chloropentyl)-1H-indole (22.2 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 (23.0 mg, 0.150 mmol) and DMF (1.00 mL), giving the desired product as a yellow oil (36 mg, 81%). 1H NMR (400 MHz, CDCl3) δ 8.08–6.52 (m, 11H), 4.19 (t, 2H, J=7.2 Hz), 3.26–3.10 (m, 2H), 2.71–2.55 (m, 2H), 2.55–2.42 (m, 2H), 2.35–2.12 (m, 2H), 2.12–1.80 (m, 6H), 1.80–1.57 (m, 2H), 1.51–1.34 (m, 2H) 1.31 (d, 6H, J=6.8 Hz); ESMS m/e: 432.2 (M+H)+.

Workup

  1. customPrepared as above,

Sources & evidence

ORD record
ord-0b459767d3814ffeb9747176d46d827c
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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