Propionyl chloride → HCID 12804786, compound

HRID 1648915Notes

Reaction equation

HRID 1648915 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1([OH:30])[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:18][CH2:17]1.C([Li])CCC.[C:36]([Cl:40])(=[O:39])[CH2:37][CH3:38]>O1CCCC1.O>[ClH:40].[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1([O:30][C:36](=[O:39])[CH2:37][CH3:38])[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 62324Propionyl chlorideHCID 13288026HCID 13288026, compoundHCID 178418339Butyllithium

Product 1

HCID 12804786HCID 12804786, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.4 g of 4-[α-(2-fluoro-4-methylphenyl)-2-tolyl]-1-phenethyl-4-piperidinol, Example 11, in 30 ml of tetrahydrofuran is cooled to -60° C. To this cooled solution is added 1.5 ml of n-butyllithium and the resulting solution stirred for 15 minutes. To this solution is added dropwise 0.3 ml of propionyl chloride at this low temperature and after total addition the solution is permitted to reach ambient temperature. The solution is stirred at ambient temperature for 24 hours. The solution is diluted with water and extracted with chloroform. The chloroform extract is dried and filtered and the chloroform evaporated off leaving a white powder. The powder is recrystallized from a methanol-acetone-ether mixture to give the product, mp 195°-197° C. of 4-[α-(2-fluoro-4-methylphenyl)-2-tolyl]-4-propionyloxy-1-phenethylpiperidine hydrochloride.

Workup

  1. additionafter total addition the solution
  2. customto reach ambient temperature
  3. stirringThe solution is stirred at ambient temperature for 24 hours
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. customis dried
  7. filtrationfiltered
  8. customthe chloroform evaporated off
  9. customleaving a white powder
  10. customThe powder is recrystallized from a methanol-acetone-ether mixture

Sources & evidence

ORD record
ord-301eb5188dd9439aaf82d4bf72300440
Source dataset
uspto-grants-1983_11
Patent number
US04414219

Reaction notes

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