Sodium Hydroxide → 2-Methyl-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalen-2-ylamine

HRID 577641Notes

Reaction equation

HRID 577641 reaction equation
[CH3:1][C:2]1(CC(N)=O)[C:14](=O)[C:5]2=[CH:6][C:7]3[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=3[CH:13]=[C:4]2[CH2:3]1.[OH-].[Na+].CC1([NH2:32])CC2C(=CC=CC=2)C1>C(O)(=O)C.OS(O)(=O)=O>[CH3:1][C:2]1([NH2:32])[CH2:14][C:5]2=[CH:6][C:7]3[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=3[CH:13]=[C:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 224992292-Methyl-2,3-dihydro-1H-inden-2-amineHCID 54404642(2-methyl-1-oxo-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalen-2-yl)-acetamide

Product 1

HCID 224991832-Methyl-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalen-2-ylamine

Reagents, catalysts & solvents 1

HCID 23350293Acetic acid sulfuric acidSolvent

Procedure

A 4:1 mixture of geometrical isomers, containing predominantly 2,2,2-trifluoro-.N.-(2-methyl-1-oxo-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalen-2-yl)-acetamide, is hydrogenated over PD/C in acetic acid/H2SO4 and the products are saponified with NaOH according to the procedures described for the preparation of 2-methyl-indan-2-ylamine. The resulting product mixture is recrystallised repeatedly from hexane to give the title compound, a single isomer.

Workup

  1. additionA 4:1 mixture of geometrical isomers
  2. additioncontaining predominantly 2,2,2-trifluoro-.N
  3. customThe resulting product mixture is recrystallised repeatedly from hexane

Sources & evidence

ORD record
ord-684edbcc1b4545ec8855a13aef443fac
Source dataset
uspto-grants-2015_05
Patent number
US09040559B2

Reaction notes

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