Triethylamine → HCID 23045638, compound

HRID 2108190Notes

Reaction equation

HRID 2108190 reaction equation
[C:1]([Cl:6])(=[O:5])[CH2:2][CH2:3][CH3:4].COC1C=[C:11]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1.[CH2:21](N(CC)CC)[CH3:22].[Cl-].[CH2:29]([NH+](CC)CC)C>C1(C)C=CC=CC=1>[ClH:6].[CH2:11]([N:15]1[CH2:16][CH2:17][CH2:18][CH:19]([C:3]2[CH:4]=[CH:22][CH:21]=[C:1]([O:5][CH3:29])[CH:2]=2)[CH2:20]1)[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 6057251-(3-Methoxyphenyl)piperidineHCID 12698378Triethylazanium chloride

Product 1

HCID 23045638HCID 23045638, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Butyryl chloride (2.0 g, 0.019 mol) in dry toluene (5 ml) was slowly added to a solution of 3-methoxyphenylpiperidine (2.45 g, 0.013 mol) and triethylamine (1.92 g, 0.013 mol) in dry toluene at 5° . The mixture was stirred at room temperature for 30 min., whereupon the triethylammonium chloride formed was filtered off and the solvent evaporated. The crude N-butyryl-3-(3-methoxyphenyl)piperidine (2.82 g) dissolved in dry tetrahydrofuran (30 ml) was added to a suspension of LiAlH4 (2.0 g) in dry tetrahydrofuran (30 ml) under nitrogen. After reflux for 3 h the mixture was hydrolysed, the precipitate filtered off and the solvent evaporated. The residue dissolved in light petroleum was passed through an alumina column. (Alternatively the residue could be distilled in vacuo.) The product was precipitated as the hydrochloride and recrystallized from ethanol/ether yielding the pure product (3.6 g, 88%) mp 130-1° C.

Workup

  1. customformed
  2. filtrationwas filtered off
  3. customthe solvent evaporated
  4. dissolutionThe crude N-butyryl-3-(3-methoxyphenyl)piperidine (2.82 g) dissolved in dry tetrahydrofuran (30 ml)
  5. additionwas added to a suspension of LiAlH4 (2.0 g) in dry tetrahydrofuran (30 ml) under nitrogen
  6. temperatureAfter reflux for 3 h the mixture
  7. filtrationthe precipitate filtered off
  8. customthe solvent evaporated
  9. dissolutionThe residue dissolved in light petroleum
  10. distillation(Alternatively the residue could be distilled in vacuo
  11. custom) The product was precipitated as the hydrochloride
  12. customrecrystallized from ethanol/ether yielding the pure product (3.6 g, 88%) mp 130-1° C.

Sources & evidence

ORD record
ord-63585f84d2d847529ec3a12f99edf50b
Source dataset
uspto-grants-1990_06
Patent number
US04937346

Reaction notes

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