2-(Benzyloxycarbonylaminomethyl)indan → (2,3-Dihydro-1H-inden-2-yl)methanamine

HRID 1654940Notes

Reaction equation

HRID 1654940 reaction equation
C(OC([NH:11][CH2:12][CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14]1)=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH2:11][CH2:12][CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14]1

Participants

5

Reactant 2

HCID 189214832-(Benzyloxycarbonylaminomethyl)indanHCID 178418361HCID 178418361, compound

Product 1

HCID 22346315(2,3-Dihydro-1H-inden-2-yl)methanamineYield 90.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10.6 g (37.7 mmol) of 2-(benzyloxycarbonylaminomethyl)indan was dissolved in 100 ml of methanol, to which 1.3 g of palladium on carbon was added and stirred for 4 hours in the stream of hydrogen. The catalyst was removed by filtration, the solvent was evaporated, and 5.04 g of 2-(aminomethyl)indan was obtained. The obtained compound was immediately dissolved in 150 ml of methylene chloride, to which 100 ml of water and 6.2 g of potassium carbonate were added, and the mixture was vigorously stirred. 8.02 g (38.0 mmol) of 4-chlorobenzenesulfonyl chloride was added thereto portionwise under ice-cooling, followed by stirring for 30 minutes. The organic phase was collected, dried and the solvent was removed by distillation. The crystalline residue was recrystallized from a solvent mixture of ethyl acetate and hexane to obtain 9.82 g of 2-[(4-chlorophenyl)sulfonylaminomethyl]indan as colorless needles. Yield: 76%

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-fafa13803e284f2abd679c86953c0d74
Source dataset
uspto-grants-1995_04
Patent number
US05409956

Reaction notes

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