1-Benzyl-4-piperidone → HCID 14391473, compound

HRID 1193955Notes

Reaction equation

HRID 1193955 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:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH4+].[Cl-]>O1CCCC1.CCOCC.BrC(Br)C>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][N:4]1[CH:5]=[CH:6][CH:7]=[C:3]1[C:26]1([OH:29])[CH2:27][CH2:28][N:23]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:24][CH2:25]1

Participants

8

Reactant 4

HCID 192201-Benzyl-4-piperidoneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 14391470HCID 14391470, compound

Product 1

HCID 14391473HCID 14391473, compoundYield 72.3%

Reagents, catalysts & solvents 3

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

Procedure

To a suspension of magnesium turnings (2.2 g, 0.09 mole) in 60 ml tetrahydrofuran (THF) and 30 ml ether, was added a few drops of a solution of 2-bromo-1-(2-fluorobenzyl)pyrrole (20 g, 0.074 mole) in 60 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 30 minutes, the mixture was cooled with an ice bath, then a solution of 1-benzyl-4-piperidone (11.2 g, 0.06 mole) in 75 ml THF was added. After stirring at ambient temperature for one hour, the mixture was poured into NH4Cl solution, then extracted with ethyl acetate. The ethyl acetate solution was washed with water, then dried over anhydrous MgSO4. After evaporation of the solvent, the resultant oil (25 g) was purified by HPLC, using ethyl acetate/hexane/diethylamine (30:70:0.5) as the eluent to give 15.8 g of 4-[1-((2-fluorophenyl)methyl)- 1H-pyrrol-2-yl]-1-benzyl-4-piperidinol, m.p. 112°-117° C.

Workup

  1. temperatureheat
  2. temperaturereflux
  3. temperatureat reflux for 30 minutes
  4. temperaturethe mixture was cooled with an ice bath
  5. stirringAfter stirring at ambient temperature for one hour
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate solution was washed with water
  8. dry with materialdried over anhydrous MgSO4
  9. customAfter evaporation of the solvent
  10. customthe resultant oil (25 g) was purified by HPLC

Sources & evidence

ORD record
ord-75502b0babeb41d4b9b2e746641f364b
Source dataset
uspto-grants-1989_03
Patent number
US04812450

Reaction notes

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