p-Toluenesulfonic acid → N-methylhex-5-en-1-amine 4-methylbenzenesulfonate

HRID 388640Notes

Reaction equation

HRID 388640 reaction equation
FC(F)(F)[C:3]([N:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])C)=O.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21]([OH:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1>CO>[S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)([OH:24])(=[O:23])=[O:22].[CH3:3][NH:5][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 575787592,2,2-Trifluoro-N-(hex-5-EN-1-YL)-N-methylacetamide

Product 1

HCID 46737741N-methylhex-5-en-1-amine 4-methylbenzenesulfonateYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At room temperature, compound 1a (71.88 g, 1 eq.) and p-toluene sulfonic acid (74.4 g, 1.2 eq.) were dissolved in MeOH (640 mL). The reaction mixture was refluxed for 7 days. The solvent was removed under vacuum and the residue was recrystallised in acetone. The product was isolated by filtration, dried on P2O5 to yield compound 2a as a white solid in 76% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.38 (quint, J=7.76 Hz, 2H), 1.71 (q, J=7.76 Hz, 2H), 1.99 (quint, J=6.98 Hz, 2H), 2.38 (s, 3H), 2.70 (t, J=5.17 Hz, 2H), 4.92-4.99 (m, 2H), 5.67-5.73 (m, 1H), 7.20 (brs, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 7 days
  2. customThe solvent was removed under vacuum
  3. customthe residue was recrystallised in acetone
  4. customThe product was isolated by filtration
  5. customdried on P2O5

Sources & evidence

ORD record
ord-6511a233791d4fc48291f1450b495e68
Source dataset
uspto-grants-2013_02
Patent number
US08377962B2

Reaction notes

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