Water → (4-(1,3-dioxolan-2-yl)phenyl)methanamine

HRID 2080121Notes

Reaction equation

HRID 2080121 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[CH:8][C:9]([CH2:10][NH2:11])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 27784284-(1,3-Dioxolan-2-yl)benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 10559254(4-(1,3-dioxolan-2-yl)phenyl)methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[1,3]Dioxolan-2-yl-benzonitrile described in Preparation Example 119 (3.78 g, 21.6 mmol) was dissolved in tetrahydrofuran (76 mL), lithium aluminum hydride (4.09 g, 108 mmol) was added at 0° C., and the solution was stirred overnight at room temperature. Water (4.09 mL), an aqueous solution of 5N sodium hydroxide (4.09 mL) and water (12.3 mL) were sequentially added to the reaction solution. The reaction solution was filtered through Celite pad, then, the filtrate was evaporated in vacuo, and the title compound (3.92 g, quantitatively) was obtained as a pale yellow oil.

Workup

  1. filtrationThe reaction solution was filtered through Celite pad
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-7ad26db0d3544d589d2ea46555e0d17c
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…