Water → HCID 14822644, compound

HRID 1032264Notes

Reaction equation

HRID 1032264 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH2:8][CH2:9][N:10]([CH3:23])[C:11]([CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1)=O.O.[OH-].[Na+]>C1COCC1>[OH:7][CH2:8][CH2:9][N:10]([CH2:11][CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1)[CH3:23]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 14822635HCID 14822635, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14822644HCID 14822644, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an incomplete solution of 7.5 g (200 mmol) of LAH in 200 ml of THF was added a solution of 30.65 g (131.4 mmol) of 1-[N-(2-hydroxyethyl)-N-methylaminocarbonyl]-1,2,3,4-tetrahydronaphthalene, a compound of Formula 11 prepared, for example, as described in Preparation 11, dissolved in 100 ml of THF. The reaction was stirred at reflux for 30 minutes, cooled to ambient temperature, and treated with 7.5 ml of water, 7.5 ml of 15% NaOH, and finally with 22.5 ml of water. Insoluble inorganic materials were removed by filtration and the filtrate concentrated to give 27.31 g of 1-[N-(2-hydroxyethyl)-N-methylaminomethyl]-1,2,3,4-tetrahydronaphthalene, an intermediate of Formula 12, as an oil.

Workup

  1. customas described in Preparation 11
  2. temperatureat reflux for 30 minutes
  3. customInsoluble inorganic materials were removed by filtration
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-b34d4317435943989b797c898a33dc0a
Source dataset
uspto-grants-1990_09
Patent number
US04957914

Reaction notes

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