Ethanol → Ethyl 1-(4-bromophenyl)piperidine-4-carboxylate

HRID 57589Notes

Reaction equation

HRID 57589 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH2:21](O)[CH3:22]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([C:14]([O:16][CH2:21][CH3:22])=[O:15])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 710936711-(4-Bromophenyl)piperidine-4-carboxylic acid

Product 1

HCID 71093667Ethyl 1-(4-bromophenyl)piperidine-4-carboxylate

Procedure

To a stirred solution of 1-(4-bromophenyl)piperidine-4-carboxylic acid (1.56 g, 5.5 mmol) in absolute ethanol (30 mL) was cooled to 0° C. and SOCl2 (1.18 g, 10 mmol) added drop-wise. The mixture was stirred to room temperature and heated to reflux for 3 hours. The reaction mixture was evaporated in vacuo and the residue dissolved in saturated aqueous solution of NaHCO3 (50 mL). The aqueous solution was extracted with EtOAc (3×30 mL). The organic extracts was dried over Na2SO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent; ethyl acetate: hexane=1:1) to yield the title compound pale brown oil 1.08 g. MS (m/z): 314 (M+2)+

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. customThe reaction mixture was evaporated in vacuo
  4. dissolutionthe residue dissolved in saturated aqueous solution of NaHCO3 (50 mL)
  5. extractionThe aqueous solution was extracted with EtOAc (3×30 mL)
  6. dry with materialThe organic extracts was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate: hexane=1:1)

Sources & evidence

ORD record
ord-af667b2eab174f76a867511ce26e2bc7
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

Loading…