Triethylamine → (R)-3-benzylpiperazin-2-one

HRID 581194Notes

Reaction equation

HRID 581194 reaction equation
C[O:2][C:3](=O)[C@H:4]([NH:12][CH2:13][CH2:14][NH2:15])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:5]([C@H:4]1[NH:12][CH2:13][CH2:14][NH:15][C:3]1=[O:2])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 54002275(2R)-2-(2-aminoethylamino)-3-phenylpropionic acid methyl ester

Product 1

HCID 16740989(R)-3-benzylpiperazin-2-oneYield 63.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R)-2-(2-Aminoethylamino)-3-phenylpropionic acid methyl ester (0.67 g; 1.49 mmol) and triethylamine (1 ml) were dissolved in methylene chloride (10 ml) and stirred for 48 hours at room temperature. The reaction mixture was evaporated and the residue was chromatographed on silica (2.5×30 cm) using a 7% solution of ammonia in ethanol/methylene chloride (1:9) as eluent to afford 0.18 g of (3R)-3-benzylpiperazin-2-one.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was chromatographed on silica (2.5×30 cm)

Sources & evidence

ORD record
ord-fcd0501296b94eeb9008f2a96e14f9e4
Source dataset
uspto-grants-1999_07
Patent number
US05919777

Reaction notes

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