1-(2-Hydroxyethyl)piperazine → 4-(2-Hydroxyethyl)piperazine-1-carboxamide

HRID 2100425Notes

Reaction equation

HRID 2100425 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.C[Si]([N:14]=[C:15]=[O:16])(C)C>C(O)(C)C>[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:15]([NH2:14])=[O:16])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 70696Trimethylsilyl isocyanate

Product 1

HCID 47425144-(2-Hydroxyethyl)piperazine-1-carboxamideYield 88.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of 1-(2-hydroxy-ethyl)-piperazine (1.95 g, 15 mmol) in isopropanol (30 mL) at rt was added trimethylsilylisocyanate (2.8 mL, 21 mmol) and the resulting solution stirred overnight before the volatiles were removed in vacuo. The residue was partitioned between CH2Cl2 and water. The aqueous phase was concentrated in vacuo to give 4-(2-hydroxy-ethyl)-piperazine-1-carboxylic acid amide (2.3 g, 88%); 1H-NMR (300 MHz, d6-DMSO) 5.92 (2H, s), 4.40 (1H, t), 3.46-3.52 (2H, m), 3.22-3.34 (4H, m), 2.30-2.39 (6H, m); m/z (ES+) 173 [M+H]+.

Workup

  1. customwere removed in vacuo
  2. customThe residue was partitioned between CH2Cl2 and water
  3. concentrationThe aqueous phase was concentrated in vacuo

Sources & evidence

ORD record
ord-b5821917fd8e45ed9f93ad4cebeb7dd4
Source dataset
uspto-grants-2009_08
Patent number
US07572794B2

Reaction notes

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