Acetyl chloride → (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide

HRID 1632565Notes

Reaction equation

HRID 1632565 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([CH3:8])[N:3]1[CH2:9][CH2:10][NH:11][C:12](=[O:21])[CH2:13][N:14]1[CH2:18][CH2:17][CH:16]([OH:19])[C:15]1=[O:20].[C:22](Cl)(=[O:24])[CH3:23]>C(Cl)(Cl)Cl>[CH3:8][C@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:2]([CH3:1])[N:3]1[CH2:9][CH2:10][NH:11][C:12](=[O:21])[CH2:13][N:14]1[CH2:18][CH2:17][CH:16]([O:19][C:22](=[O:24])[CH3:23])[C:15]1=[O:20]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 3069833cis-(+-)-N-(2-(2,6-Dimethyl-1-piperidinyl)ethyl)-2-oxo-3-hydroxy-1-pyrrolidineacetamide

Product 1

HCID 53715870(R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.0 g of (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide are heated to reflux for 3 hours in 60 ml of chloroform and 1.5 ml of acetyl chloride. After evaporation of the volatile constituents, the residue is treated three times with toluene and in each case again evaporated in vacuo. The residue is chromatographed over aluminum oxide (activity grade III, neutral). The (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide which is extracted with chloroform has a melting point of 121°-122° after recrystallization from diethyl ether.

Workup

  1. customAfter evaporation of the volatile constituents
  2. additionthe residue is treated three times with toluene
  3. customin each case again evaporated in vacuo
  4. customThe residue is chromatographed over aluminum oxide (activity grade III, neutral)
  5. extractionThe (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide which is extracted with chloroform
  6. customafter recrystallization from diethyl ether

Sources & evidence

ORD record
ord-c39b4fb9c77e4c4eaa0187b0a4a2bfe5
Source dataset
uspto-grants-1984_10
Patent number
US04476308

Reaction notes

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