Ammonium Chloride → HCID 14391478, compound

HRID 1193956Notes

Reaction equation

HRID 1193956 reaction equation
[Mg].Br[C:3]1[N:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[CH:5]=[CH:6][CH:7]=1.[CH2:16]([N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1)[CH2:17][CH2:18][CH3:19].[NH4+].[Cl-]>O1CCCC1.CCOCC.BrC(Br)C>[CH2:16]([N:20]1[CH2:25][CH2:24][C:23]([C:3]2[N:4]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[F:15])[CH:5]=[CH:6][CH:7]=2)([OH:26])[CH2:22][CH2:21]1)[CH2:17][CH2:18][CH3:19]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 899951-Butyl-4-piperidoneHCID 5462224MagnesiumHCID 14391470HCID 14391470, compound

Product 1

HCID 14391478HCID 14391478, compoundYield 34.3%

Reagents, catalysts & solvents 3

HCID 112011,1-DibromoethaneCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of magnesium turnings (1.0 g, 0.04 mole) in 25 ml tetrahydrofuran (THF) and 10 ml ether, was added a few drops of a solution of 2-bromo-1-(2-fluorobenzyl)pyrrole (10 g, 0.04 mole) in 35 ml THF. The reaction was initiated with a few drops of dibromoethane and heat, and reflux was maintained by the addition of the bromo compound. After stirring at reflux for thirty minutes, the mixture was cooled with an ice-bath, then a solution of 1-butyl-4-piperidone (4.6 g, 0.03 mole) in 25 ml THF was added. After stirring at ambient temperature for one hour, the mixture was poured into an NH4Cl solution, then extracted with ether. The ether solution was washed with water, then dried over anhydrous MgSO4. After evaporation of the solvent, the resultant oil (11 g) was purified by HPLC using ethyl acetate as the eluent to give 3.4 g of 1-butyl-4-[1-(2-fluorobenzyl)pyrrol-2-yl]-4-piperidinol; m.p. 132°-5° C.

Workup

  1. temperatureheat
  2. temperaturereflux
  3. temperatureat reflux for thirty minutes
  4. temperaturethe mixture was cooled with an ice-bath
  5. stirringAfter stirring at ambient temperature for one hour
  6. extractionextracted with ether
  7. washThe ether solution was washed with water
  8. dry with materialdried over anhydrous MgSO4
  9. customAfter evaporation of the solvent
  10. customthe resultant oil (11 g) was purified by HPLC

Sources & evidence

ORD record
ord-02d20504535d463a9aaa7b0f9930bf73
Source dataset
uspto-grants-1989_03
Patent number
US04812450

Reaction notes

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