Dimethylformamide → HCID 57880864, compound

HRID 1817095Notes

Reaction equation

HRID 1817095 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]N(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

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 116481324-(3,4-Dibromo-benzyl)-piperazine-1-carboxylic acid phenylamide

Product 1

HCID 57880864HCID 57880864, compound

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 Mel (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. additionwas treated with Mel (0.005 mL)
  2. stirringwas stirred at rt for 12 h
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by column chromatography (5% MeOH/DCM)

Sources & evidence

ORD record
ord-d00f4d623f4e4a22af1db8a41f0ad48f
Source dataset
uspto-grants-2009_10
Patent number
US07598249B2

Reaction notes

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