تفاعل #329872

ord-b57d5ff52afe4dbbae5895aac90f5ebb

معادلة التفاعل

Clc1ccc(Br)cc1
4-chlorobromobenzene
C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1
3-(R)-Methyl-piperazine-1-carboxylic acid tert-butyl ester
c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1
BINAP
CC(C)(C)[O-].[Na+]
sodium-t-butoxide
C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(Cl)cc1
title compound
C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(Cl)cc1
4-(4-Chloro-phenyl)-3-(R)-methyl-piperazine-1-carboxylic acid tert-butyl ester

المذيبات

ظروف التفاعل

درجة الحرارة
110°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe solvent was evaporated
  2. 2
    غسيلwashed with saturated aqueous sodium bicarbonate and brine
  3. 3
    تجفيفdried over magnesium sulfate

الإجراء التجريبي

To a mixture of 4-chlorobromobenzene (0.53 g, 2.75 mmol) and 3-(R)-Methyl-piperazine-1-carboxylic acid tert-butyl ester (0.5 g, 2.5 mmol) in toluene (20 mL) was added tris(dibenzylideneacetone) dipalladium(0) (0.029 g, 0.032 mmol), BINAP (0.058 g, 0.093 mmol) and sodium-t-butoxide (1.01 g, 10.5 mmol). The resulting mixture was heated 110° C. for 20 h. The solvent was evaporated and the residue was taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate and brine and dried over magnesium sulfate. Column chromatography (10% ethyl acetate/hexane) provided the title compound.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08653096B2uspto-grants-2014_02