Sodium Bicarbonate → 1-(3,5-Dicyclopropylpyridin-2-yl)piperazine

HRID 2411218Notes

Reaction equation

HRID 2411218 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([CH:20]3[CH2:22][CH2:21]3)=[CH:18][C:17]([CH:23]3[CH2:25][CH2:24]3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH:20]1([C:19]2[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[N:15][CH:16]=[C:17]([CH:23]3[CH2:25][CH2:24]3)[CH:18]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 673807934-(3,5-Dicyclopropylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 584847011-(3,5-Dicyclopropylpyridin-2-yl)piperazineYield 87.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The intermediate 4-(3,5-dicyclopropylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (7.4 g) described in Preparation Example 87 was dissolved in chloroform (54 mL), 4N hydrogen chloride/ethyl acetate (22 mL) was added, and the mixture was stirred at room temperature overnight. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, the mixture was extracted with chloroform, and the solvent was evaporated to give the title compound (4.6 g).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f8416423081f4517beeabb2ea6c2bd69
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

Loading…