Hydrochloric Acid → Methyl-piperidin-4-yl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine

HRID 1426372Notes

Reaction equation

HRID 1426372 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([N:17]([CH3:27])[C:18]2[S:19][C:20]([C:23]([F:26])([F:25])[F:24])=[N:21][N:22]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.Cl>O>[CH3:27][N:17]([CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)[C:18]1[S:19][C:20]([C:23]([F:26])([F:24])[F:25])=[N:21][N:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 593235704-[Methyl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amino]-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 59323568Methyl-piperidin-4-yl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amineYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-[M ethyl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amino]-piperidine-1-carboxylic acid benzyl ester (D1) (0.91 g, 2.27 mmol) in a solution 6 N of hydrochloric acid (15 ml) was stirred at 150° C. for 10 min., under microwave irradiation. After cooling to room temperature, the reaction mixture was diluted with water and extracted with dichloromethane (25 ml). The aqueous layer was basified with a saturated solution of sodium carbonate and extracted with dichloromethane (3×25 ml). The combined organic extracts were dried (Na2SO4) and the solvent evaporated in vacuo to yield D2 (0.56 g, 93%) as a solid. C9H13F3N4S requires 266. Found 266 (MH+).

Workup

  1. extractionextracted with dichloromethane (25 ml)
  2. extractionextracted with dichloromethane (3×25 ml)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-cd163e0a52b04b64966deef784f17112
Source dataset
uspto-grants-2015_01
Patent number
US08933101B2

Reaction notes

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