Ammonium Chloride → HCID 14391477, compound

HRID 1193954Notes

Reaction equation

HRID 1193954 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.[Cl:16][C:17]1[CH:31]=[CH:30][C:20]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]2)=[CH:19][CH:18]=1.[NH4+].[Cl-]>O1CCCC1.CCOCC.BrC(Br)C>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][C:26]([C:3]3[N:4]([CH2:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[F:15])[CH:5]=[CH:6][CH:7]=3)([OH:29])[CH2:27][CH2:28]2)=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 11959626HCID 11959626, compoundHCID 14391470HCID 14391470, compound

Product 1

HCID 14391477HCID 14391477, compoundYield 51.9%

Reagents, catalysts & solvents 3

HCID 112011,1-DibromoethaneCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

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 (10.0 g, 0.04 mole) in 30 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-(4-chlorophenethyl)-4-piperidone (5.0 g, 0.021 mole) was added. After stirring at ambient temperature for one hour, the mixture was poured into a solution of NH4Cl, then extracted with ether. The ether solution was washed with water, then dried over anhydrous MgSO4. After evaporation of the solvent, the resultant oil, 12 g, was purified by high pressure liquid chromatography (HPLC), using ethyl acetate as the eluent to give 4.5 g of 1-(4-chlorophenethyl)-4-[1-(2-fluorobenzyl)pyrrol-2-yl]-4-piperidinol, m.p. 108°-9° 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 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, 12 g, was purified by high pressure liquid chromatography (HPLC)

Sources & evidence

ORD record
ord-b1020003ca30495cbfde7bff4ef71404
Source dataset
uspto-grants-1989_03
Patent number
US04812450

Reaction notes

Loading…