N-[(5,6-dimethoxyindan-2-yl)methylcarbonyl]-N-(methyl)amine → [2-(5,6-dimethoxy-2,3-dihydro-1H-inden-2-yl)ethyl]methylamine

HRID 487560Notes

Reaction equation

HRID 487560 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][CH:7]([CH2:14][C:15]([NH:17][CH3:18])=O)[CH2:6]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[CH2:6][CH:7]([CH2:14][CH2:15][NH:17][CH3:18])[CH2:8]2

Participants

4

Reactant 2

HCID 19092185N-[(5,6-dimethoxyindan-2-yl)methylcarbonyl]-N-(methyl)amineHCID 21226445Aluminium lithium hydride

Product 1

HCID 68533314[2-(5,6-dimethoxy-2,3-dihydro-1H-inden-2-yl)ethyl]methylamineYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

37 g of N-[(5,6-dimethoxyindan-2-yl)methylcarbonyl]-N-(methyl)amine are treated with 8.5 g of LiAlH4 in 470 ml of tetrahydrofuran under reflux for 6 hours, then the mixture is hydrolysed and subsequently concentrated to yield, finally, 24 g of N-[(5,6-dimethoxyindan-2-yl)-ethyl)-N-(methyl)amine (yield 69%).

Workup

  1. temperatureunder reflux for 6 hours
  2. concentrationsubsequently concentrated
  3. customto yield

Sources & evidence

ORD record
ord-532af7af33f749608edf7fd885d66852
Source dataset
uspto-grants-1994_03
Patent number
US05296482

Reaction notes

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