Ethyl Acetate → HCID 67366133, compound

HRID 1500320Notes

Reaction equation

HRID 1500320 reaction equation
[C:1](Cl)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C([N:19]1[CH2:24][CH2:23][C:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:21][CH2:20]1)C1C=CC=CC=1.C(OCC)(=O)C>C(Cl)(Cl)Cl>[CH2:4]([O:3][C:1]([N:19]1[CH2:20][CH2:21][C:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:23][CH2:24]1)=[O:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 67367347HCID 67367347, compound

Product 1

HCID 67366133HCID 67366133, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

60 g (3.5 eq) Cbz chloride were added dropwise to a solution of 33 g (1 eq) 1-benzyl-4-phenyl-4-(pyrrolidin-1-yl)piperidine in 330 ml chloroform over a period of 10 min and the reaction mixture obtained was stirred for 30 min at room temperature. The reaction course was monitored by thin-layer chromatography (ethyl acetate). Once the conversion was complete, the solvent was distilled off completely and the residue adjusted to a pH of ˜6 with 10% HCl solution and washed 3 times with 100 ml EtOAc. In an ice bath the aqueous solution was adjusted to a pH of ˜9 with NaOH solution and then extracted 3 times with 100 ml chloroform. The combined organic phases were dried with Na2SO4. Following removal of the solvent under reduced pressure, the residue was purified by column chromatography (silica gel; 20% EtOAc/heptane). 11 g (29%) of product were obtained in the form of a yellow solid.

Workup

  1. customthe reaction mixture obtained
  2. distillationthe solvent was distilled off completely
  3. washwashed 3 times with 100 ml EtOAc
  4. customIn an ice bath the aqueous solution was adjusted to a pH of ˜9 with NaOH solution
  5. extractionextracted 3 times with 100 ml chloroform
  6. dry with materialThe combined organic phases were dried with Na2SO4
  7. customremoval of the solvent under reduced pressure
  8. customthe residue was purified by column chromatography (silica gel; 20% EtOAc/heptane)

Sources & evidence

ORD record
ord-3dac2108b91f41849af028febf8606dc
Source dataset
uspto-grants-2015_12
Patent number
US09206156B2

Reaction notes

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