Hydrochloric Acid → (1R)-1-[6-(Trifluoromethyl)(3-pyridyl)]ethylamine

HRID 1257517Notes

Reaction equation

HRID 1257517 reaction equation
CC(S([NH:7][C@@H:8]([C:10]1[CH:11]=[N:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=1)[CH3:9])=O)(C)C.Cl>CO>[F:18][C:16]([F:17])([F:19])[C:13]1[N:12]=[CH:11][C:10]([C@H:8]([NH2:7])[CH3:9])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 581035742-methyl-N-{(1R)-1-[6-(trifluoromethyl)-3-pyridinyl]ethyl}-2-propanesulfinamide

Product 1

HCID 55278063(1R)-1-[6-(Trifluoromethyl)(3-pyridyl)]ethylamineYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-N-{(1R)-1-[6-(trifluoromethyl)-3-pyridinyl]ethyl}-2-propanesulfinamide (41.6 g, 141 mmol) in methyl alcohol (470 mL) at 0° C. was added hydrogen chloride (4.0 M in dioxane; 106 mL, 424 mmol). After 30 min, the mixture was concentrated to dryness. The residue was recrystallized using ethyl alcohol (15 mL) and ether (40 mL). The white solid was filtered and dried under reduced pressure to give the hydrochloride salt of the title compound (26.3 g). MS191.2 (M+1). 1H NMR (500 MHz, CD3 OD): δ 8.83 (d, J=2.2 Hz, 1H); 8.17 (d, J=8.2 Hz, 1H); 7.93 (d, J=8.2 Hz, 1H); 4.69 (q, J=6.9 Hz, 1H); 1.70 (d, J=6.9 Hz, 3H).

Workup

  1. concentrationthe mixture was concentrated to dryness
  2. customThe residue was recrystallized
  3. filtrationThe white solid was filtered
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-80b10afb57bd4cd395d297f67807f313
Source dataset
uspto-grants-2013_06
Patent number
US08461185B2

Reaction notes

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