Hydrochloric Acid → Azabuperone

HRID 2083675Notes

Reaction equation

HRID 2083675 reaction equation
[N:1]12[CH2:9][CH2:8][CH2:7][CH:6]1[CH2:5][NH:4][CH2:3][CH2:2]2.[I-].[K+].[OH-].[K+].C[O:15][C:16](OC)([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[CH2:17][CH2:18][CH2:19]Cl.Cl.[OH-].[NH4+]>C(Cl)Cl.C(O)C.C(OCC)C.O>[N:1]12[CH2:9][CH2:8][CH2:7][CH:6]1[CH2:5][N:4]([CH2:19][CH2:18][CH2:17][C:16]([C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1)=[O:15])[CH2:3][CH2:2]2

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 14923Ammonium HydroxideHCID 558578Octahydropyrrolo(1,2-a)pyrazineHCID 112766731-(4-CHLORO-1,1-DIMETHOXYBUTYL)-4-FLUOROBENZENE

Product 1

HCID 18484AzabuperoneYield 49%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a heated slurry of 2.90 parts of 1,4-diazabicyclo[4.3.0]nonane, 1.91 parts of potassium iodide, and 25 parts of deionized water is added 1.65 parts potassium hydroxide and 6.17 parts of 1,1-dimethoxy-1-(4-fluorophenyl)-4-chlorobutane under nitrogen. The mixture is heated to reflux and held at that temperature for 4.5 hours. After cooling to room temperature, 18 parts of ethyl ether and a sufficient quantity of concentrated hydrochloric acid to bring the pH of the aqueous phase to about 2 are added. The aqueous layer is separated and basified to pH 12 with 50% sodium hydroxide solution. The resultant oil which forms is extracted into chloroform. The solvent is removed under reduced pressure to afford an orange oil. Chromatography of this oil using silica gel as an adsorbant and mixtures of ethanol (0.5 - 20%) in methylene chloride with 0.25% ammonium hydroxide as eluants affords 4-(1,4-diazabicyclo[4.3.0]non-4-yl)-4'-fluorobutyrophenone as an orange oil, in yield of 49%. This compound is represented by the following structural formula. ##STR18##

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. additionare added
  4. customThe aqueous layer is separated
  5. extractionThe resultant oil which forms is extracted into chloroform
  6. customThe solvent is removed under reduced pressure
  7. customto afford an orange oil

Sources & evidence

ORD record
ord-7a30966111994072a1965b4325449210
Source dataset
uspto-grants-1978_04
Patent number
US04086234

Reaction notes

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