N-bromobutanimide → HCID 58817714, compound

HRID 2111709Notes

Reaction equation

HRID 2111709 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[C:23]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:24]=3[S:25][CH:26]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>C(Cl)(Cl)(Cl)Cl>[C:9]([O:13][C:14]([N:16]1[CH2:17][CH2:18][N:19]([C:22]2[C:23]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:24]=3[S:25][C:26]=2[Br:1])[CH2:20][CH2:21]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58817658HCID 58817658, compound

Product 1

HCID 58817714HCID 58817714, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In an alternative procedure, add N-bromosuccinimide (1.319 g, 6.62 mmol) to a stirring solution of 4-(6-fluoro-benzo[b]thiophen-3-yl)-piperazine-1-carboxylic acid tert-butyl ester (Example 46a) (2.226 g, 6.62 mmol) in CCl4 and reflux for 2 h. Allow cooling to room temperature and filter. Evaporate the solvent and purify the residue by chromatography over silica gel (EtOAc/heptane, 9:1) to obtain 2.34 g (94%) of oil.

Workup

  1. temperaturereflux for 2 h
  2. filtrationfilter
  3. customEvaporate the solvent
  4. custompurify the residue by chromatography over silica gel (EtOAc/heptane, 9:1)

Sources & evidence

ORD record
ord-4e84fd0f8c544b3ea328a78130358d51
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

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