Propane sultone → 1,2,3,4-Tetrahydroquinoline-N-propanesulphonic acid

HRID 1837405Notes

Reaction equation

HRID 1837405 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:11]1[CH2:17][S:14](=[O:16])(=[O:15])[O:13][CH2:12]1>C(#N)C>[S:14]([CH2:17][CH2:11][CH2:12][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)([OH:16])(=[O:15])=[O:13]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 92497391,2,3,4-Tetrahydroquinoline-N-propanesulphonic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1,2,3,4-tetrahydroquinoline (4.76 g, 40 mmole) and 1,3-propane sultone (4.88 g, 40 mmole) in 50 mL reagent grade acetonitrile was heated under a nitrogen atmosphere and refluxed overnight. After cooling to room temperature, then to ice bath temperature, the resulting white solid was filtered and washed with cold acetonitrile. The yield was 8.1 g (84%), and the product had a melting point of greater than 200° C. Nuclear magnetic resonance (NMR) and elemental analysis showed the product to be consistent with the assigned structure. NMR (D2O): 7.45 (s, 4H), 2.8-4.0 (m, 8H), 2.2 (T, 2H).

Workup

  1. temperaturewas heated under a nitrogen atmosphere
  2. temperaturerefluxed overnight
  3. filtrationto ice bath temperature, the resulting white solid was filtered
  4. washwashed with cold acetonitrile

Sources & evidence

ORD record
ord-e210f35d5463487ea86536b784277169
Source dataset
uspto-grants-2004_08
Patent number
US06783731B1

Reaction notes

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