HCID 13935588, compound → HCID 13935589, compound

HRID 232169Notes

Reaction equation

HRID 232169 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5](S(C1C=CC(C)=CC=1)(=O)=O)[CH2:6][CH2:7][C:8]([F:12])([F:11])[CH2:9][NH2:10]>Br>[F:11][C:8]([F:12])([CH2:9][NH2:10])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3][CH2:2][NH2:1]

Participants

3

Reactant 1

HCID 13935588HCID 13935588, compound

Product 1

HCID 13935589HCID 13935589, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

The 1,8-diamino-4-p-toluenesulfonyl-7,7-difluoro-4-aza-octane so obtained is refluxed with 100 mL of 48% aqueous HBr for 20 hours. After cooling to room temperature, the solution is carefully extracted with ether (5×300 mL). After evaporation of the solvent, traces of free HBr are removed by stripping twice with water; on stripping with ethanol, the desired 7,7-difluoro-1,8-diamino-aza-octane crystallizes as the trihydrobromide. Digestion with acetone yields white crystals which are washed with acetone, a small amount of ethanol, and finally with ether: 12.85 g (95%).

Workup

  1. extractionthe solution is carefully extracted with ether (5×300 mL)
  2. customAfter evaporation of the solvent, traces of free HBr
  3. customare removed
  4. customthe desired 7,7-difluoro-1,8-diamino-aza-octane crystallizes as the trihydrobromide
  5. customDigestion with acetone yields white crystals which
  6. washare washed with acetone

Sources & evidence

ORD record
ord-15cffd874e4042a1904ba4e72e745858
Source dataset
uspto-grants-1989_07
Patent number
US04851448

Reaction notes

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