Propane sultone → HCID 19861525, compound

HRID 1165987Notes

Reaction equation

HRID 1165987 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.[CH2:12]1[S:16](=[O:18])(=[O:17])[O:15][CH2:14][CH2:13]1>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:14][CH2:13][CH2:12][S:16]([OH:18])(=[O:17])=[O:15])[CH2:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 14264Propane sultone2×HCID 147839116-Fluoro-1,2,3,4-tetrahydroquinoline

Product 1

HCID 19861525HCID 19861525, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
150 °C

Procedure

To 6,05 g (40 mMol) 6-fluoro-1,2,3,4-tetrahydroquinoline in 20 ml acetone, 5.9 g (48 mMol) of propane sultone dissolved in 20 ml acetone are added dropwise for a period of 40 minutes at 50° to 60° C. After 24 hours of refluxing and again after 48 hours a further 5.9 g of propane sultone are added. After a total of 60 hours of refluxing, the reaction mixture is concentrated by evaporation and the volatile components are removed in high vacuum (0.01 torr) by heating to about 150° C. The residue is recrystallized from 115 ml methanol.

Workup

  1. additionare added dropwise for a period of 40 minutes at 50° to 60° C
  2. additionare added
  3. temperatureAfter a total of 60 hours of refluxing
  4. concentrationthe reaction mixture is concentrated by evaporation
  5. customthe volatile components are removed in high vacuum (0.01 torr)
  6. customThe residue is recrystallized from 115 ml methanol

Sources & evidence

ORD record
ord-0f0aa5ac86c0422eb3924e36521b3533
Source dataset
uspto-grants-1990_03
Patent number
US04912258

Reaction notes

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