1-Methylpiperazine → HCID 60128253, compound

HRID 2307447Notes

Reaction equation

HRID 2307447 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.ClCCl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:22]2[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]2)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 531671-MethylpiperazineHCID 62657Potassium Phosphate, TribasicHCID 56971804(S)-N-Boc-1-(3-bromophenyl)ethylamine

Product 1

HCID 60128253HCID 60128253, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of (S)-[1-(3-bromophenyl)ethyl]carbamic acid tert-butyl ester (5.0 g, 16.7 mmol), 1-methylpiperazine (6.7 g, 67 mmol), Pd2(dba)3 (1.55 g, 10 mol %), di-t-butyl-biphenylphosphine (0.51 g, 10 mol %), potassium phosphate (7.2 g, 34 mmol) in ethylene glycol dimethyl ether (40 ml) was refluxed for 4 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane (100 mL) and the precipitate was filtered off. The filtrate was concentrated under vacuum. The crude product was purified by flash chromatography over silica with ethyl acetate/hexanes (1:1) to provide (S)-{1-[3-(4-methylpiperazin-1-yl)phenyl]ethyl}carbamic acid tert-butyl ester as an oil (3.4 g, 64% yield).

Workup

  1. temperaturewas refluxed for 4 hours
  2. filtrationthe precipitate was filtered off
  3. concentrationThe filtrate was concentrated under vacuum
  4. customThe crude product was purified by flash chromatography over silica with ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-1faa2a4134904fbba9812fd3d012a027
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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