Potassium Carbonate → (5-Bromo-3-methyl-pyridin-2-yl)-(2-pyrrolidin-1-yl-ethyl)-amine

HRID 1916745Notes

Reaction equation

HRID 1916745 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:9]=[C:10]([CH3:23])[C:11]([NH:14][C:15](=O)[CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:12][CH:13]=1.[OH-].[Na+].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]([CH3:23])[C:11]([NH:14][CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)=[N:12][CH:13]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67362705N-(5-bromo-3-methyl-pyridin-2-yl)-2-pyrrolidin-1-yl-acetamide

Product 1

HCID 67363857(5-Bromo-3-methyl-pyridin-2-yl)-(2-pyrrolidin-1-yl-ethyl)-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere 2 mL of a 1 M solution of LiAlH4 in THF are slowly added dropwise to a solution, cooled to 0° C., of 800 mg (2.68 mmol) N-(5-bromo-3-methyl-pyridin-2-yl)-2-pyrrolidin-1-yl-acetamide (Example 15b) in 10 mL THF and the reaction mixture is stirred for 3 h at this temperature. 20% NaOH is slowly added dropwise, solid K2CO3 is added to the suspension and this is stirred vigorously. The precipitate is filtered off, the filtrate is evaporated down and the residue is purified by chromatography (silica gel, EtOAc/MeOH/NH3 80:20:2).

Workup

  1. stirringthis is stirred vigorously
  2. filtrationThe precipitate is filtered off
  3. customthe filtrate is evaporated down
  4. customthe residue is purified by chromatography (silica gel, EtOAc/MeOH/NH3 80:20:2)

Sources & evidence

ORD record
ord-359e1a44d2f74d83a869723bca6eca16
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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