Hydrochloric Acid → HCID 86735493, compound

HRID 616769Notes

Reaction equation

HRID 616769 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[N+:17]([O-:19])=[O:18])[O:9][CH2:8][CH2:7][O:6]1.[OH:20][C:21]1([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].[ClH:43]>[I-].[K+].C(C(C)=O)C(C)C>[ClH:43].[OH:20][C:21]1([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:34])[F:35])[CH:28]=2)[CH2:26][CH2:25][N:24]([CH2:2][CH2:3][CH2:4][C:5]2([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[N+:17]([O-:19])=[O:18])[O:9][CH2:8][CH2:7][O:6]2)[CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 752554-[3-(Trifluoromethyl)phenyl]-4-piperidinolHCID 713856872-(3-Bromopropyl)-2-(4-fluoro-2-nitrophenyl)-1,3-dioxolane

Product 1

HCID 86735493HCID 86735493, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4-bromo-1-(4-fluoro-2-nitrophenyl)-1,1-ethylenedioxy-n-butane (3.3 g), 4-hydroxy-4-(3-trifluoromethylphenyl)piperidine (1.96 g), potassium carbonate (1.1 g), potassium iodide (20 mg) and methyl isobutyl ketone (25 g) was heated under refluxing for one hour. To the resulting mixture, 13% hydrochloric acid (8.2 g) was added under cooling, and the precipitated crystals were collected by filtration, washed with toluene and dried to give 3.9 g (91.1%) of 4-[4-hydroxy-4-(3-trifluoromethylphenyl)piperidino]-1-(4-fluoro-2-nitrophenyl)-1,1-ethylenedioxy-n-butane hydrochloride. M.P. 229° C (decomp.).

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for one hour
  3. temperatureunder cooling
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with toluene
  6. customdried

Sources & evidence

ORD record
ord-4a0955b60a64436e9ea0927d9fdc419b
Source dataset
uspto-grants-1978_02
Patent number
US04075346

Reaction notes

Loading…