Ethyl Acetate → HCID 67366133, compound

HRID 2387951Notes

Reaction equation

HRID 2387951 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 equiv.) of Cbz chloride were added dropwise over a period of 10 minutes to a solution of 33 g (1 equiv.) of 1-benzyl-4-phenyl-4-(pyrrolidin-1-yl)piperidine in 330 ml of chloroform, and the resulting reaction mixture was stirred for 30 minutes at room temperature. The progress of the reaction was monitored by thin-layer chromatography (ethyl acetate). When the reaction was complete, the solvent was distilled off completely and the residue was adjusted to ˜pH 6 with 10% HCl solution and washed 3× with 100 ml of EtOAc. In an ice bath, the aqueous solution was adjusted to ˜pH 9 with NaOH solution and then extracted 3× with 100 ml of chloroform. The combined organic phases were dried with Na2SO4. After removal of the solvent under reduced pressure, purification was carried out 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 resulting reaction mixture
  2. distillationthe solvent was distilled off completely
  3. washwashed 3× with 100 ml of EtOAc
  4. customIn an ice bath, the aqueous solution was adjusted
  5. extractionextracted 3× with 100 ml of chloroform
  6. dry with materialThe combined organic phases were dried with Na2SO4
  7. customAfter removal of the solvent
  8. customunder reduced pressure, purification

Sources & evidence

ORD record
ord-159fc92ba8014464958e56c946da96c6
Source dataset
uspto-grants-2012_09
Patent number
US08269000B2

Reaction notes

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