Hydrochloric Acid → HCID 69353998, compound

HRID 1836415Notes

Reaction equation

HRID 1836415 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.[ClH:47]>C(O)(C)C>[ClH:47].[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

5

Reactant 3

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

Product 1

HCID 69353998HCID 69353998, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-(3-nitrobenzoyl)-1-trifluoromethylcarbonylpiperidine (4.9 g (0.0148 mol)) and 4-(2-nitrobenzoyl)-1-trifluoromethylcarbonylpiperidine (67:33) were added to isopropanol (100 mL) and HCl 37% (15 mL). The suspension was refluxed for 10 h to complete the hydrolysis. The reaction was monitored by TLC [silica gel/ethyl acetate-hexane (2:3)]. The resulting yellow solution was allowed to cool to room temperature and the resulting suspension was post-agitated for 10 h. The reaction mixture was then concentrated under reduce pressure and the residue was dried under vacuum for 16 h at 50° C. 4 g (100%) of 4-(3-nitrobenzoyl)piperidine HCl and 4-(2-nitrobenzoyl)piperidine HCl mixture were isolated as a light colored solid.

Workup

  1. temperatureThe suspension was refluxed for 10 h
  2. customthe hydrolysis
  3. concentrationThe reaction mixture was then concentrated
  4. customthe residue was dried under vacuum for 16 h at 50° C

Sources & evidence

ORD record
ord-6e7a501e847447fe9087bd25d5afa505
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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