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

HRID 517023Notes

Reaction equation

HRID 517023 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 31a (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 then removed under vacuum, and the residue was recrystallized in acetone. The product was isolated by filtration and dried over P2O5 to give compound 32a as a white powder in 76% yield. 1H NMR (CDCl3, 400 MHz): δ (ppm) 1.38 (q, J=7.76 Hz, 2H), 1.71 (q, J=7.76 Hz, 2H), 1.99 (q, J=6.98 Hz, 2H), 2.38 (s, 3H), 2.70 (t, J=5.17 Hz, 3H), 2.87-2.93 (m, 2H), 4.92-4.99 (m, 2H), 5.67-5.73 (m, 1H), 7.20 (d, J=7.76 Hz, 2H), 7.75 (d, J=7.76 Hz, 2H), 8.62 (br s, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 7 days
  2. customThe solvent was then removed under vacuum
  3. customthe residue was recrystallized in acetone
  4. customThe product was isolated by filtration
  5. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-badf21e947c94035835f06a62dd2a86f
Source dataset
uspto-grants-2015_08
Patent number
US09115095B2

Reaction notes

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