Methyl iodide → HCID 57880864, compound

HRID 1754213Notes

Reaction equation

HRID 1754213 reaction equation
[C:1]1([NH:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Br:23])=[C:19]([Br:24])[CH:18]=3)[CH2:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:27]I>CN(C=O)C>[CH3:27][N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]([N:10]1[CH2:11][CH2:12][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[C:19]([Br:24])[CH:18]=2)[CH2:14][CH2:15]1)=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 116481324-(3,4-Dibromo-benzyl)-piperazine-1-carboxylic acid phenylamide

Product 1

HCID 57880864HCID 57880864, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(3,4-dibromo-benzyl)-piperazine-1-carboxylic acid phenylamide (0.02 g) in DMF (0.6 mL) was added NaH (60% dispersion in oil; 3 mg) in one portion. The resulting mixture was allowed to stir for 30 min, then was treated with MeI (0.005 mL), and was stirred at rt for 12 h. The mixture was concentrated and the residue was purified by column chromatography (5% MeOH/DCM), giving the product as a white solid (0.015 g). 1H NMR (400 MHz, CDCl3): 7.54-7.50 (m, 2H), 7.33-7.31 (m, 2H), 7.12-7.05 (m, 4H), 3.34 (s, 2H), 3.22-3.20 (m, 6H), 2.23-2.21 (m, 4H), 1.63 (s, 3H).

Workup

  1. stirringwas stirred at rt for 12 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by column chromatography (5% MeOH/DCM)

Sources & evidence

ORD record
ord-7e644f4d3ce04f658496edec5027d4de
Source dataset
uspto-grants-2015_10
Patent number
US09169224B2

Reaction notes

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