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

HRID 1804008Notes

Reaction equation

HRID 1804008 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 6212ChloroformSolvent2×

Procedure

4-(3,5-Dicyclopropylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (7.4 g), which is the intermediate described in Preparation Example 50, was dissolved in chloroform (54 mL), 4N hydrogen chloride/ethyl acetate (21.5 mL) was added, and the mixture was stirred at room temperature overnight. To the reaction mixture was added chloroform and saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with chloroform. The solvent was evaporated to give the title compound (4.6 g).

Workup

  1. customdescribed in Preparation Example 50
  2. extractionthe mixture was extracted with chloroform
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4cda58c60d654b7fbd9cc25a01bc8114
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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