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

HRID 1087078Notes

Reaction equation

HRID 1087078 reaction equation
[I-].ClC1C=CC=C[N+]=1C.[C:10]([O:13][CH:14]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]([OH:22])=O)[C:15]1=[O:23])(=[O:12])[CH3:11].[CH3:24][C@H:25]1[CH2:30][CH2:29][CH2:28][C@@H:27]([CH3:31])[N:26]1[CH2:32][CH2:33][NH2:34].C(N(CC)CC)C>C(Cl)Cl>[CH3:24][C@H:25]1[CH2:30][CH2:29][CH2:28][C@@H:27]([CH3:31])[N:26]1[CH2:32][CH2:33][NH:34][C:20](=[O:22])[CH2:19][N:16]1[CH2:17][CH2:18][CH:14]([O:13][C:10](=[O:12])[CH3:11])[C:15]1=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 7837022-(cis-2,6-Dimethyl-1-piperidinyl)ethanamineHCID 54389912(R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetic acid

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 6344DichloromethaneSolvent2×

Procedure

1.81 g of 2-chloro-1-methyl-pyridinium iodide are suspended in 10 ml of methylene chloride and thereto there are added at room temperature 1.20 of (R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetic acid. Within 15 minutes there is added dropwise at 0° a solution of 0.98 g of 94.7% cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine and 3.02 ml of triethylamine in 20 ml of methylene chloride, whereupon the mixture is stirred at room temperature for 18 hours. Thereupon, the mixture is evaporated and the residue is chromatographed on aluminum oxide (activity grade III, neutral). The material which is eluted with chloroform is chromatographed on silica gel (granular size 0.2-0.5 mm). The (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrroldinyl)acetamide which is eluted with alcohol has a melting point of 120°-122° after crystallization from diethyl ether.

Workup

  1. customThereupon, the mixture is evaporated
  2. customthe residue is chromatographed on aluminum oxide (activity grade III, neutral)
  3. washThe material which is eluted with chloroform
  4. customis chromatographed on silica gel (granular size 0.2-0.5 mm)
  5. washThe (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrroldinyl)acetamide which is eluted with alcohol
  6. customafter crystallization from diethyl ether

Sources & evidence

ORD record
ord-9f4a1819d2ab4f38b4153282682472f8
Source dataset
uspto-grants-1991_07
Patent number
US05034402

Reaction notes

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