N-bromobutanimide → HCID 15678883, compound

HRID 1085428Notes

Reaction equation

HRID 1085428 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([O:12][C:13]1[CH:14]=[CH:15][C:16]2[N:23]([CH3:24])[CH:22]3[CH2:25][CH:18]([CH2:19][CH2:20][N:21]3[CH3:26])[C:17]=2[CH:27]=1)(=[O:11])[CH3:10].C(=O)(O)[O-].[Na+]>CO.ClCCl>[C:9]([O:12][C:13]1[CH:14]=[C:15]([Br:1])[C:16]2[N:23]([CH3:24])[CH:22]3[CH2:25][CH:18]([CH2:19][CH2:20][N:21]3[CH3:26])[C:17]=2[CH:27]=1)(=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 15678881HCID 15678881, compound

Product 1

HCID 15678883HCID 15678883, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

N-Bromosuccinimide (2.40 g) was added in three portions to a solution of 3.50 g of crude 1,2,3,4,5,6-hexahydro-1,3-dimethyl-2,6-methano-1,3-benzodiazocin-8-ol acetate in 135 ml of deoxygenated methanol. The resulting solution was stirred at room temperature for five minutes and then diluted with dichloromethane and a saturated sodium bicarbonate solution. The aqueous phase was separated and extracted with dichloromethane, and the combined organic layers were washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to an oil. Column chromatography of the oil (silica gel elution with triethylamine-methanol-ethyl acetate) afforded 1.80 g (33%) of 10-bromo-1,2,3,4,5,6-hexahydro-1,3-dimethyl-2,6-methano-1,3-benzodiazocine-8-ol acetate as a solid.

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted with dichloromethane
  3. washthe combined organic layers were washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. washColumn chromatography of the oil (silica gel elution with triethylamine-methanol-ethyl acetate)

Sources & evidence

ORD record
ord-840b0bf2425d4697aee21e8ab8cfea5f
Source dataset
uspto-grants-1991_04
Patent number
US05010083

Reaction notes

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