Hydrochloric Acid → Hydrochloric Acid

HRID 511127Notes

Reaction equation

HRID 511127 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:15][C:16]([F:25])([F:24])[C:17]1[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[ClH:40]>ClC(Cl)C.ClCCl.C(OCC)C>[ClH:40].[NH:8]1[CH2:9][CH2:10][CH:11]([NH:23][C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:24])[F:25])[CH:18]=2)[CH2:12][CH2:13]1.[ClH:40]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 73753-(Trifluoromethyl)anilineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 313Hydrochloric AcidHCID 66681328HCID 66681328, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (500 mg; 2.51 mmol), 3-trifluoromethyl-phenylamine (404 mg; 2.51 mmol) and sodium triacetoxyborohydride (1.59 g; 7.53 mmol) are suspended in dichloroethane (25 mL). After 1 day reaction time at room temperature, the mixture is diluted with dichloromethane (100 mL) and the organic layer is washed with aq. sat ammonium chloride (2×50 mL) and water (3×50 mL), is then dried over magnesium sulfate and is concentrated under reduced pressure. The residue obtained is triturated with cold diethylether (10 mL) until precipitation is observed. The precipitate is filtered and dried under vacuum. The crude product is dissolved in dichloromethane (5 mL) and trifluoroacetic acid (5 mL) is added dropwise under vigorous stirring. After 30 minutes reaction time, the mixture is concentrated under reduced pressure and co-evaporated with dichloromethane (2×10 mL). The residue obtained is then dissolved in diethylether (5 mL) and a molar solution of hydrochloric acid in diethylether (5 mL) is added. The precipitate formed is filtered and dried under high vacuum to afford the desired product as hydrochloride (289 mg; 1.03 mmol).

Workup

  1. customAfter 1 day reaction time at room temperature
  2. washthe organic layer is washed
  3. dry with materialis then dried over magnesium sulfate
  4. concentrationis concentrated under reduced pressure
  5. customThe residue obtained
  6. customis triturated with cold diethylether (10 mL) until precipitation
  7. filtrationThe precipitate is filtered
  8. customdried under vacuum
  9. dissolutionThe crude product is dissolved in dichloromethane (5 mL)
  10. additiontrifluoroacetic acid (5 mL) is added dropwise under vigorous stirring
  11. customAfter 30 minutes reaction time
  12. concentrationthe mixture is concentrated under reduced pressure and co-evaporated with dichloromethane (2×10 mL)
  13. customThe residue obtained
  14. customThe precipitate formed
  15. filtrationis filtered
  16. customdried under high vacuum

Sources & evidence

ORD record
ord-fbb88137e8db44e7be49ebe2b731c347
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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