p-Toluenesulfonic acid monohydrate → HCID 86635740, compound

HRID 1919803Notes

Reaction equation

HRID 1919803 reaction equation
[CH3:1][C:2]([NH2:14])([C:4]1[CH:5]=[N:6][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:9]=1)[CH3:3].O.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([OH:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(OC)(C)(C)C.O1CCCC1>[C:16]1([CH3:26])[CH:17]=[CH:18][C:19]([S:22]([OH:25])(=[O:23])=[O:24])=[CH:20][CH:21]=1.[CH3:3][C:2]([NH2:14])([C:4]1[CH:5]=[N:6][C:7]([C:10]([F:12])([F:13])[F:11])=[CH:8][CH:9]=1)[CH3:1]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 545799022-[6-(Trifluoromethyl)pyridin-3-yl]propan-2-amine

Product 1

HCID 86635740HCID 86635740, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
18 °C

Procedure

Add a solution of 1-Methyl-1-(6-trifluoromethyl-pyridin-3-yl)-ethylamine (280 g, 1.37 moles) in methyl t-butyl ether (1.4 L) to a solution of p-toluenesulfonic acid monohydrate (212.5 g, 1.23 moles) in tetrahydrofuran (980 mL). Observe a pH of 2.0 and an exotherm to 28° C. Cool to 18° C. and filter solids. Rinse filter cake with methyl t-butyl ether (1.4 L). Vacuum dry the filter cake at ambient temperature and collect 408 g (79%) of the titled compound as a white solid. 1H NMR (DMSO-d6, 500 MHz): δ 8.94 (d, 1H, J=2.5), 8.53 (br s, 3H), 8.2 (dd, 1H, J=5.5, 8), 8.02 (d, 1H, J=8), 7.46 (d, 2H, J=8), 7.10 (d, 2H, J=7.5), 2.27 (s, 3H), 1.68 (s, 6H).

Workup

  1. customto 28° C
  2. filtrationfilter solids
  3. washRinse
  4. filtrationfilter cake with methyl t-butyl ether (1.4 L)
  5. customVacuum dry the filter cake at ambient temperature
  6. customcollect 408 g (79%) of the titled compound as a white solid

Sources & evidence

ORD record
ord-ab56a993fe144770999b331ac14a3eca
Source dataset
uspto-grants-2012_05
Patent number
US08168659B2

Reaction notes

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