1,2-Dichloroethane → Piperidin-4-yl benzoate

HRID 2171658Notes

Reaction equation

HRID 2171658 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.ClCCCl.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])O.[Na+]>CCOC(C)=O>[C:19]([O:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 12416427Piperidin-4-yl benzoateYield 101.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-hydroxypiperidine-1-carboxylate (3.0 g) was mixed with DCE (30 ml), and TEA (3.0 ml) and benzoyl chloride (2.4 g) was added thereto, followed by stirring at room temperature for 1 hour. A saturated aqueous sodium hydrogen carbonate solution and EtOAc were added to the reaction mixture, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was mixed with DCE (30 ml), and TFA (10 ml) was added thereto, followed by stirring at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and then the residue was purified by basic silica gel column chromatography (CHCl3/MeOH) to obtain piperidin-4-yl benzoate (3.1 g).

Workup

  1. additionwas added
  2. dry with materialthe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. additionThe obtained residue was mixed with DCE (30 ml), and TFA (10 ml)
  5. additionwas added
  6. stirringby stirring at room temperature for 5 hours
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. customthe residue was purified by basic silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-45af65e5dfc047deb55591d05b036400
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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