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

HRID 1289438Notes

Reaction equation

HRID 1289438 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>CO.[C].[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

4

Reactant 1

HCID 189214832-(Benzyloxycarbonylaminomethyl)indan

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Dissolved in 100 ml of methanol were 10.6 g (37.7 mmol) of 2-(benzyloxycarbonylaminomethyl)indane, and 1.3 g of 10% palladium-carbon were added to the solution. The mixture was stirred for 4 hours under a hydrogen atmosphere. After separating the catalyst by filtration, the solvent was distilled off to obtain 5.04 g of 2-(aminomethyl)indane. This compound was immediately dissolved in 150 ml of methylene chloride, and 100 ml of water and 6.2 g of potassium carbonate were added to the solution, followed by vigorous stirring of the resultant mixture. While chilling with ice water, 8.02 g (38.0 mmol) of 4-chlorobenzenesulfonyl chloride were added in small portions. Thereafter, the mixture was stirred for 30 minutes. After an organic layer separated was taken out and dried, the solvent was distilled out of the organic layer. The resultant crystalline residue was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain 9.82 g of 2-[(4-chlorophenyl)sulfonylaminomethyl]indane as a colorless needle crystal. Yield: 76%.

Workup

  1. additionwere added to the solution
  2. customAfter separating the catalyst
  3. filtrationby filtration
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-83094693f0764df48850efefe4de9562
Source dataset
uspto-grants-1998_05
Patent number
US05750524

Reaction notes

Loading…