Sodium Iodide → HCID 67974683, compound

HRID 1777604Notes

Reaction equation

HRID 1777604 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.[CH:24]1([CH2:30][NH2:31])[CH2:29][CH2:28][CH2:27][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][C:18]([CH2:21][NH:31][CH2:30][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 76688CyclohexanemethylamineHCID 67974260HCID 67974260, compound

Product 1

HCID 67974683HCID 67974683, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-((cyclohexylmethylamino)methyl)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), cyclohexylmethanamine (0.120 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 0.061 g (71%) of the title compound as a white solid.

Workup

  1. customN-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-((cyclohexylmethylamino)methyl)benzamide was prepared

Sources & evidence

ORD record
ord-f3a047c3b91948b1ac758956363286c4
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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