Hydrochloric Acid → HCID 69353998, compound

HRID 1836413Notes

Reaction equation

HRID 1836413 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 54%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-(3-nitrobenzoyl)-1-trifluoromethylcarbonylpiperidine and 4-(2-nitrobenzoyl)-1-trifluoromethylcarbonylpiperidine [67(m):33(o)] mixture (40.36 g, 0.122 mol) was heated with reflux in isopropanol (1.39 L) containing HCl 37% (209 mL) for 18 h. The reaction was monitored by TLC [silica gel/ethyl acetate-hexane (2:3)]. The resulting solution was allowed to cool to room temperature and the crystallization occurred at Tmass=35° C. Then the suspension was post-agitated for 3 h at room temperature. The precipitate was collected by filtration, washed with ethanol (100 mL) and ethyl ether (100 mL) and dried under vacuum at 50° C. to give pure 4-(3-nitrobenzoyl)piperidine HCl as a pale yellow solid (17.81 g, 54%).

Workup

  1. customthe crystallization
  2. customoccurred at Tmass=35° C
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with ethanol (100 mL) and ethyl ether (100 mL)
  5. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-7d44c8ff798141ac8886e6a51ca81b8e
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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