Hydrochloric Acid → 4-n-Butyl-1-[4-(2-hydroxyphenyl)-4-oxo-1-butyl]piperidine

HRID 1723890Notes

Reaction equation

HRID 1723890 reaction equation
[CH2:1]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22]CC2C=CC=CC=2)=[O:15])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].Cl.[OH-].[Na+].C(Cl)Cl.CO>CCO.[Pd]>[CH2:1]([CH:5]1[CH2:6][CH2:7][N:8]([CH2:11][CH2:12][CH2:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[OH:22])=[O:15])[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 186263744-n-Butyl-1-[4-(2-benzyloxyphenyl)-4-oxo-1-butyl]piperidineHCID 21226129Dichloromethane methanol

Product 1

HCID 99264764-n-Butyl-1-[4-(2-hydroxyphenyl)-4-oxo-1-butyl]piperidineYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-n-Butyl-1-[4-(2-hydroxyphenyl)-4-oxol-butyl]piperidine (27)-3 To a 25 mL reaction flask was added a solution of 4-n-Butyl-1-[4-(2-benzyloxyphenyl)-4-oxo-1-butyl]piperidine (26) (49 mg, 1.2 mmol) dissolved in dry EtOH (10 mL) and conc. HCl (0.1 mL) followed by addition of palladium on charcoal (40 mg). The reaction flask was then charged with H2 by the use of balloon technique and left stirring at rt over-night under H2 atmosphere. The reaction mixture was basified by addition of NaOH (2 mL, 2.0 M) and filtered through celite. The aqueous phase was extracted with ethyl acetate (3×50 mL) and the combined organic phases were washed with brine (10 mL) and NaOH (10 mL, 2 M), dried (MgSO4) and evaporated to dryness to produce 0.42 g of crude 27. The crude product was subjected to CC [eluent: : CH2Cl2: MeOH (99:1)] to give pure 27 (0.21 g, 58%); LC-MS [M+H]+ 303 (cald. 303.2).

Workup

  1. additionThe reaction flask was then charged with H2 by the use of balloon technique
  2. waitleft
  3. filtrationfiltered through celite
  4. extractionThe aqueous phase was extracted with ethyl acetate (3×50 mL)
  5. washthe combined organic phases were washed with brine (10 mL) and NaOH (10 mL, 2 M)
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. customto produce 0.42 g of crude 27

Sources & evidence

ORD record
ord-d3faa60d54944562a28a281ffaaf6aa1
Source dataset
uspto-grants-2009_02
Patent number
US07485651B2

Reaction notes

Loading…