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

HRID 1906278Notes

Reaction equation

HRID 1906278 reaction equation
[C:1]([O:4][CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([OH:13])=O)[C:6]1=[O:14])(=[O:3])[CH3:2].[CH3:15][C@H:16]1[CH2:21][CH2:20][CH2:19][C@@H:18]([CH3:22])[N:17]1[CH2:23][CH2:24][NH2:25]>O1CCCC1>[CH3:15][C@H:16]1[CH2:21][CH2:20][CH2:19][C@@H:18]([CH3:22])[N:17]1[CH2:23][CH2:24][NH:25][C:11](=[O:13])[CH2:10][N:7]1[CH2:8][CH2:9][CH:5]([O:4][C:1](=[O:3])[CH3:2])[C:6]1=[O:14]

Participants

4

Reactant 2

HCID 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 8028TetrahydrofuranSolvent

Procedure

1.0 g of (R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetic acid is placed in 15 ml of absolute tetrahydrofuran, whereupon 0.89 g of N,N'-carbonyldiimidazole is added in one portion. The mixture is stirred at room temperature until the gas evolution is complete. Thereafter, 0.86 g of 94.7% cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine is added and the mixture is left to stand overnight at room temperature and then evaporated. The residue is chromatographed on 60 g of 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 eluted with methylene chloride has a melting point of 121°-122° after trituration with diethyl ether.

Workup

  1. additionis added in one portion
  2. waitthe mixture is left
  3. customevaporated
  4. customThe residue is chromatographed on 60 g of aluminum oxide (activity grade III, neutral)
  5. washThe (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide which is eluted with methylene chloride

Sources & evidence

ORD record
ord-ed97e6919f67452e962da5f9e172bbfb
Source dataset
uspto-grants-1987_03
Patent number
US04650878

Reaction notes

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