Diethyl Ether → 2,3-Dihydro-N-methyl-1H-indene-1-methanamine

HRID 1032266Notes

Reaction equation

HRID 1032266 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC.[CH3:12][NH:13][C:14]([CH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17]1)=O.[OH-].[Na+]>O.C1COCC1>[CH3:12][NH:13][CH2:14][CH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 14822650N-methyl-2,3-dihydro-1H-indene-1-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 148226602,3-Dihydro-N-methyl-1H-indene-1-methanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4.0 g (0.1M) of LAH and 400 ml of ether was stirred while a solution of 9.0 g (51 mmol) of 1-methylaminocarbonyl-indane, a compound of Formula 13 prepared, for example, as described in Preparation 13, dissolved 200 ml of THF was added over a period of 30 minutes. The reaction mixture was stirred and heated to reflux for 6 hours, and then stirred at ambient temperature for an additional 16 hours. The reaction mixture was then digested by treating dropwise with water, 15% NaOH, and then water, yielding 1-methylaminomethyl-indane, an intermediate amine of Formula 14; (HCl salt, ethanol-ether, mp 169°-171° C.).

Workup

  1. customas described in Preparation 13
  2. additionwas added over a period of 30 minutes
  3. temperatureheated
  4. temperatureto reflux for 6 hours
  5. stirringstirred at ambient temperature for an additional 16 hours

Sources & evidence

ORD record
ord-9cc8092191fb43e5915975df6667c484
Source dataset
uspto-grants-1990_09
Patent number
US04957914

Reaction notes

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