Piperazine → [1-(4-Chlorobenzyl)-2-oxo-2-piperazin-1-yl-ethyl]-carbamic acid tert-butyl ester

HRID 1192292Notes

Reaction equation

HRID 1192292 reaction equation
[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:2]([C:11]([OH:13])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[C:17]([O:16][C:14](=[O:15])[NH:1][CH:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:10])=[CH:8][CH:9]=1)[C:11](=[O:13])[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 4837PiperazineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7018791N-Boc-4-chloro-D-phenylalanine

Product 1

HCID 67538094[1-(4-Chlorobenzyl)-2-oxo-2-piperazin-1-yl-ethyl]-carbamic acid tert-butyl esterYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc-D-Phe(4-Cl)—OH (3.65 g, 12.2 mmol), piperazine (10 g, 116 mmol) in DCM (200 mL) were added HOBT (3.3 g, 24 mmol) and EDCI (4.7 g, 25 mmol). The mixture was stirred at room temperature for 12 hours. The solution was washed with water, brine and dried over magnesium sulfate. After filtration, the organic solvent was evaporated and the residue was subject to silica gel chromatography to afford the product [1-(4-chlorobenzyl)-2-oxo-2-piperazin-1-yl-ethyl]-carbamic acid tert-butyl ester (0.58 g, 13%). 1H NMR (CDCl3, 400 Hz) δ 7.25 (d, J=8.4 Hz, 2H), 7.12 (d, J=8.0 Hz, 2H), 5.52 (d, J=8.4 Hz, 1H), 4.83-4.77 (m, 1H), 3.63-3.45 (m, 2H), 3.37-3.32 (m, 1H), 3.08-3.04 (m, 1H), 2.99-2.90 (m, 2H), 2.81-2.70 (m, 3H), 2.42-2.38 (m, 1H), 1.41 (s, 9H). MS (ESI+) [M+H]+ 369.

Workup

  1. washThe solution was washed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtration
  4. customthe organic solvent was evaporated

Sources & evidence

ORD record
ord-5d923d2ba4a04f179acf8f8e1619c929
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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