Sodium Iodide → HCID 67974572, compound

HRID 1777606Notes

Reaction equation

HRID 1777606 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][C:18]([CH2:21]Cl)=[CH:17][CH:16]=1.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[I-].[Na+]>C1COCC1>[CH2:24]([NH:31][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]([NH:13][CH2:12][CH2:11][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=3)[NH:7][CH:6]=2)=[O:23])=[CH:16][CH:17]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 7504BenzylamineHCID 67974260HCID 67974260, compound

Product 1

HCID 67974572HCID 67974572, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-((Benzylamino)methyl)-N-(2-(5-chloro-1H-indol-3-yl)ethyl)benzamide was prepared following Method C starting from N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-(chloromethyl)benzamide (0.070 g; 0.202 mmol), benzylamine (0.0997 mL; 0.907 mmol) and sodium iodide (0.153 g; 1.01 mmol) in THF (3 mL), under a microwave irradiation at 150° C. for 5 minutes. Flash chromatography on silica gel (eluent 2 to 10% methanol in dichloromethane) furnished 0.051 g (61%) of the title compound as a white solid.

Workup

  1. custom4-((Benzylamino)methyl)-N-(2-(5-chloro-1H-indol-3-yl)ethyl)benzamide was prepared

Sources & evidence

ORD record
ord-b1af2e352a61401790899ca621827af3
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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