Water → HCID 14822622, compound

HRID 1032263Notes

Reaction equation

HRID 1032263 reaction equation
[CH3:1][N:2]([CH2:16][CH:17]([O:20][CH3:21])[O:18][CH3:19])[C:3]([CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>CCOCC>[CH3:1][N:2]([CH2:3][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6]1)[CH2:16][CH:17]([O:20][CH3:21])[O:18][CH3:19]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 14822613HCID 14822613, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14822622HCID 14822622, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1-[N-methyl-N-(2,2-dimethoxyethyl)aminocarbonyl]-6-methoxy-indane 3.5 g (12 mmol), an amidoacetal compound of Formula 5, was dissolved in 20 ml of ether and added to 1.0 g (26 mmol) of LAH in 100 ml of ether. The reaction mixture was stirred at ambient temperature for 48 hours and then treated dropwise with 1 ml of water, 1 ml of 15% NaOH, and finally 3 ml of water. The insoluble inorganic materials were removed by filtration and the filtrate was concentrated to give the 3.1 g of 1-[N-methyl-N-(2,2-dimethoxyethyl)aminomethyl]-6-methoxy-indane, an aminoacetal of Formula 6, which is used without further purification.

Workup

  1. customThe insoluble inorganic materials were removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9301cb7f1f874dba999b1b1bb6482554
Source dataset
uspto-grants-1990_09
Patent number
US04957914

Reaction notes

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