Hydrochloric Acid → 4-Butylpiperidine

HRID 1293097Notes

Reaction equation

HRID 1293097 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl.CCCCCCC.CCOC(C)=O>[Pd].C(O)C>[CH2:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 149666561-Benzyl-4-butylidenepiperidineHCID 21899848Ethylacetate heptane

Product 1

HCID 132838674-ButylpiperidineYield 33%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 500 mL flask fitted with a stirrer was added a slurry of 2 (13.2 g, 58 mmol) and 10% palladium on charcoal (1.2 g) in ethanol (70 mL), followed by addition of concentrated hydrochloric acid (1.5 mL). The reaction flask was evacuated and hydrogen was added via a reaction flask. A total of 2.5 dm3 of hydrogen was consumed. The reaction mixture was filtered and evaporated and the residue was dissolved in H2O (40 mL) and NaOH (20 mL, 2 M) followed by extraction with ethyl acetate (3×100 mL). The combined organic phases were washed with brine (30 mL) and evaporated to dryness to produce 7.1 g of crude 3. The crude product was subjected to column chromatography (eluent:heptane:EtOAc (4:1)) to give pure 3 (2.7 g, 33%). 1H NMR (CDCl3) δ 0.85 (t, 3H), 1.0–1.38 (m, 9H), 1.65 (dd, 2H), 2.38 (s, 1H), 2.55 (dt, 2H), 3.04 (dt, 2H).

Workup

  1. customIn a 500 mL flask fitted with a stirrer
  2. customThe reaction flask was evacuated
  3. additionhydrogen was added via a reaction flask
  4. customA total of 2.5 dm3 of hydrogen was consumed
  5. filtrationThe reaction mixture was filtered
  6. customevaporated
  7. dissolutionthe residue was dissolved in H2O (40 mL)
  8. extractionNaOH (20 mL, 2 M) followed by extraction with ethyl acetate (3×100 mL)
  9. washThe combined organic phases were washed with brine (30 mL)
  10. customevaporated to dryness
  11. customto produce 7.1 g of crude 3

Sources & evidence

ORD record
ord-97136bb3c73645eb93951c43ccf45813
Source dataset
uspto-grants-2007_07
Patent number
US07238713B2

Reaction notes

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