Sodium Iodide → HCID 67974582, compound

HRID 1777599Notes

Reaction equation

HRID 1777599 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21]Cl)[CH:16]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.[I-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:16]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8083MorpholineHCID 67974165N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-(chloromethyl)benzamide

Product 1

HCID 67974582HCID 67974582, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-(morpholinomethyl)benzamide was prepared following Method C starting from N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-(chloromethyl)benzamide (0.050 g; 0.144 mmol), morpholine (0.046 mL; 0.5 mmol) and sodium iodide (0.153 g; 1.01 mmol) in THF (3 mL), under a microwave irradiation at 150° C. for 10 minutes. Flash chromatography on silica gel (eluent 0 to 5% methanol in dichloromethane) furnished 0.044 g (76%) of the title compound as a white solid.

Workup

  1. customN-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-(morpholinomethyl)benzamide was prepared

Sources & evidence

ORD record
ord-5c2b71070a5d4fa9adf82068d23c2638
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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