Ammonium Chloride → HCID 14698741, compound

HRID 1709851Notes

Reaction equation

HRID 1709851 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]([N:12]1[CH2:17][CH2:16][CH:15]([C:18](=[O:26])[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)(=[O:11])[CH3:10].[Cl-].[NH4+]>C(OCC)C.O1CCCC1.O>[C:9]([N:12]1[CH2:13][CH2:14][CH:15]([C:18]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[OH:26])[CH2:16][CH2:17]1)(=[O:11])[CH3:10]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 1172571-Acetyl-4-(4-fluorobenzoyl)piperidineHCID 178418255HCID 178418255, compound

Product 1

HCID 14698741HCID 14698741, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution (667 ml, 2 mole) phenylmagnesium bromide* (3 molar in ethyl ether) was diluted with 2 liters of anhydrous ethyl ether, cooled to 0°-10° C., and treated with a solution of 148 g (0.6 mole) of 1-acetyl-4-(p-fluorobenzoyl)piperidine in 1.5 liters of anhydrous tetrahydrofuran dropwise over a 1.5 hr period. The mixture was stirred at ambient temperature overnight and then poured into a solution of 107 g (2 mole) of ammonium chloride in 2 liters of cold water. The mixture was extracted thrice with 1 liter portions of benzene. The combined extracts were washed with water, dried over magnesium sulfate, and concentrated to give a semi-solid as residue. The semi-solid was triturated with isopropyl ether and the mass crystallized. The solid was collected by filtration and dried to yield 87.8 g (45%) of title compound as a white solid. An analytical sample was recrystallized from 2-propanol, mp 173°-175° C.

Workup

  1. temperaturecooled to 0°-10° C.
  2. extractionThe mixture was extracted thrice with 1 liter portions of benzene
  3. washThe combined extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give a semi-solid as residue
  7. customThe semi-solid was triturated with isopropyl ether
  8. customthe mass crystallized
  9. filtrationThe solid was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-1fa005ec70954b60a8664d038b11dd94
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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