Benzyl Bromide → HCID 53682744, compound

HRID 1534813Notes

Reaction equation

HRID 1534813 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:18][C:17]3[CH2:16][NH:15][CH2:14][CH2:13][C:12]=3[CH2:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH-].[Na+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[CH2:22]([CH:16]1[NH:15][CH2:14][CH2:13][C:12]2[CH2:11][N:10]([S:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:19])=[CH:6][CH:5]=3)(=[O:8])=[O:9])[CH2:18][C:17]1=2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 199082542,3,4,5,6,7-Hexahydro-2-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[3,4-c]pyridine

Product 1

HCID 53682744HCID 53682744, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.8 g of N8 -(p-toluenesulfonyl)-3,8-diazabicyclo[4.3.0]non-1(6)-ene, prepared in preparation 8, was dissolved in 30 ml of methanol. 6 ml of 50% aqueous sodium hydroxide solution and 1.5 ml of benzyl bromide were added to the solution and stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure to remove methanol and then extracted with methylene chloride (30 ml×3). It was dried (Na2SO4) and concentrated and then dried under reduced pressure. 2 g of the title compound was obtained (yield 85%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove methanol
  3. extractionextracted with methylene chloride (30 ml×3)
  4. dry with materialIt was dried (Na2SO4)
  5. concentrationconcentrated
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-1d44a7817b5843e890055204f6a842e8
Source dataset
uspto-grants-1992_02
Patent number
US05091384

Reaction notes

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