Hydrochloric Acid → HCID 69353998, compound

HRID 1836414Notes

Reaction equation

HRID 1836414 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=1)[C:7]([CH:9]1[CH2:14][CH2:13][N:12](C(C(F)(F)F)=O)[CH2:11][CH2:10]1)=[O:8])([O-:3])=[O:2].[N+](C1C=CC=CC=1C(C1CCN(C(C(F)(F)F)=O)CC1)=O)([O-])=O.[N+](C1C=CC(C(C2CCN(C(C(F)(F)F)=O)CC2)=O)=CC=1)([O-])=O.[ClH:70]>C(O)(C)C>[ClH:70].[N+:1]([C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=1)[C:7]([CH:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1)=[O:8])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14920262HCID 14920262, compoundHCID 14920263HCID 14920263, compoundHCID 23499233HCID 23499233, compound

Product 1

HCID 69353998HCID 69353998, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 2.8 g (8.48 mol) of 4-(3-nitrobenzoyl)-1-trifluoromethylcarbonylpiperidine, 4-(2-nitrobenzoyl)-1-trifluoromethylcarbonylpiperidine, and 4-(4-nitrobenzoyl)-1-trifluoromethylcarbonylpiperidine mixture (62:33:5) in isopropanol (60 mL) was added HCl 37% (10 mL). The reaction mixture was refluxed for 8 h and rapidly a complete dissolution was observed. Then, the solution was allowed to cool to room temperature and post-agitated for 4 h. The precipitate was filtered, rinsed with isopropanol (2×5 mL) and ethyl ether (5 mL). Drying under vacuum at 50° C. afforded pure 4-(3-nitrobenzoyl)piperidine HCl (956 mg, 42%).

Workup

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. dissolutionrapidly a complete dissolution
  3. filtrationThe precipitate was filtered
  4. washrinsed with isopropanol (2×5 mL) and ethyl ether (5 mL)
  5. customDrying under vacuum at 50° C.

Sources & evidence

ORD record
ord-9774ab39a1c54f92a5ede0361c2551a4
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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