Sodium Hydroxide → 4-(6-(4-Isopropylpiperazin-1-yl)-pyridin-3-yl)-benzylamine

HRID 80896Notes

Reaction equation

HRID 80896 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:21]=[CH:20][C:19]([C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)([CH3:9])[CH3:8].[OH-].[Na+]>C1COCC1>[CH:7]([N:10]1[CH2:11][CH2:12][N:13]([C:16]2[N:21]=[CH:20][C:19]([C:22]3[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[CH2:14][CH2:15]1)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58006673HCID 58006673, compound

Product 1

HCID 580066964-(6-(4-Isopropylpiperazin-1-yl)-pyridin-3-yl)-benzylamineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A mixture of a 1 M solution of LiAlH4 in THF (1.1 mL, 1.1 mmol) and dry THF (10 mL) was placed under an atmosphere of nitrogen. A solution of 4-(6-(4-isopropylpiperazin-1-yl)pyridin-3-yl)benzonitrile (306 mg, 1.0 mmol, prepared as described in Example 10) in dry THF (5 mL) was added dropwise. The reaction mixture was then stirred at rt for 3 h and quenced with 1 N NaOH. The mixture was filtered and the volatiles were removed. The residue was re-evaporated with THF to give 310 mg (100%) of 4-(6-(4-isopropylpiperazin-1-yl)pyridin-3-yl]benzylamine.

Workup

  1. filtrationThe mixture was filtered
  2. customthe volatiles were removed
  3. customThe residue was re-evaporated with THF

Sources & evidence

ORD record
ord-37f6402e5e3140119b42061f085d1353
Source dataset
uspto-grants-2014_09
Patent number
US08846677B2

Reaction notes

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