N-bromobutanimide → HCID 11539010, compound

HRID 2235292Notes

Reaction equation

HRID 2235292 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[NH2:9][C:10]1[C:11]([Cl:30])=[C:12]([C:26]([Cl:29])=[CH:27][CH:28]=1)[CH2:13][CH:14]1[CH2:18][CH2:17][N:16]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:15]1=[O:25]>C(Cl)(Cl)(Cl)Cl>[NH2:9][C:10]1[C:11]([Cl:30])=[C:12]([C:26]([Cl:29])=[CH:27][C:28]=1[Br:8])[CH2:13][CH:14]1[CH2:18][CH2:17][N:16]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[C:15]1=[O:25]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59299405HCID 59299405, compound

Product 1

HCID 11539010HCID 11539010, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Add NBS (7.82 g, 43.9 mmol) to a solution of 3-(3-amino-2,6-dichlorobenzyl)-1-cyclohexyl-pyrrolidin-2-one (Example 50) (15.0 g, 43.9 mmol) in CCl4 (500 mL). Stir at room temp overnight. Filter the suspension. Concentrate the filtrate. Form a suspension in CH2Cl2 and filter. Dissolve the solid in CH2Cl2 and wash several times with water. Dry, filter and concentrate. Concentrate the filtrate. Purify the combined residue by a plug of silica gel eluting with a mixture of EtOAc and hexanes (20:80) to give the title compound (17.6 g, 96%): Mass spectrum (apci) m/z=421.1 (M+H).

Workup

  1. filtrationFilter the suspension
  2. concentrationConcentrate the filtrate
  3. filtrationForm a suspension in CH2Cl2 and filter
  4. dissolutionDissolve the solid in CH2Cl2
  5. washwash several times with water
  6. customDry
  7. filtrationfilter
  8. concentrationconcentrate
  9. concentrationConcentrate the filtrate
  10. customPurify the combined residue by a plug of silica gel eluting
  11. additionwith a mixture of EtOAc and hexanes (20:80)

Sources & evidence

ORD record
ord-095a3202ec854c6ea82a750278d96481
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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