Triethylamine → HCID 20155445, compound

HRID 2413782Notes

Reaction equation

HRID 2413782 reaction equation
Cl.CO[C:4]1[CH:5]=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[OH-:16].[Na+].[CH2:18](N(CC)CC)C.[C:25]([Cl:29])(=O)[CH2:26][CH3:27].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC.O1CCCC1>[ClH:29].[CH3:18][O:16][C:7]1[CH:8]=[CH:9][CH:4]=[CH:5][C:6]=1[CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([CH2:25][CH2:26][CH3:27])[CH2:11]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 62324Propionyl chlorideHCID 199872553-(3-Methoxyphenyl)piperidine hydrochlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 20155445HCID 20155445, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

(+)-3-(3-Methoxyphenyl)piperidine hydrochloride (1.5 g, 0.0066 mol) was treated with 2 N NaOH (50 ml) and the free amine was extracted with ether. After drying (K2CO3), filtering and evaporation the residual free amine oil (1.2 g) was dissolved in dry ether (50 ml) and the triethylamine (1.4 ml, 0.0010 mol) was added. Then propionyl chloride (0.87 ml, 0.0010 mol) dissolved in dry ether (5 ml) was slowly added at 0° under stirring, and the mixture was stirred at room temperature for 30 min. The precipitate was filtered off and the solvent was evaporated giving an oily residue. This residue was dissolved in dry tetrahydrofuran (50 ml) and added to a suspension of LiAlH4 (0.75 g, 0.0020 mol) in dry tetrahydrofuran (75 ml) under N2. After refluxing for 4 h. the mixture was hydrolysed, the precipitate was filtered off and the solvent was evaporated. The residue was dissolved in ether and passed through an alumina column with ether as eluant. Addition of HCl saturated ethanol, evaporation of the solvent and recrystallization gave (-)-3-(methoxyphenyl)-N-n-propylpiperidine hydrochloride (1.48 g. 83%), 200,5°-202° C.; [α]22D -6.7 (C 2.1, CH3OH).

Workup

  1. extractionthe free amine was extracted with ether
  2. dry with materialAfter drying (K2CO3)
  3. filtrationfiltering
  4. customevaporation the residual free amine oil (1.2 g)
  5. dissolutionwas dissolved in dry ether (50 ml)
  6. additionwas slowly added at 0°
  7. stirringthe mixture was stirred at room temperature for 30 min
  8. filtrationThe precipitate was filtered off
  9. customthe solvent was evaporated
  10. customgiving an oily residue
  11. temperatureAfter refluxing for 4 h. the mixture
  12. filtrationthe precipitate was filtered off
  13. customthe solvent was evaporated
  14. dissolutionThe residue was dissolved in ether
  15. additionAddition of HCl saturated ethanol, evaporation of the solvent and recrystallization

Sources & evidence

ORD record
ord-fc1e317a31824bfd9de98cc18e5561a2
Source dataset
uspto-grants-1988_01
Patent number
US04719219

Reaction notes

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