Cyclohexylamine → 3-(Cyclohexylamino)-2,3-dihydro-1H-inden-1-one

HRID 2275314Notes

Reaction equation

HRID 2275314 reaction equation
Br[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3]1.[CH:12]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C1C=CC=CC=1>[CH:12]1([NH:18][CH:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:11])[CH2:3]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 117459123-Bromo-1-indanone

Product 1

HCID 426148023-(Cyclohexylamino)-2,3-dihydro-1H-inden-1-oneYield 84%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Bromo-2,3-dihydro-1H-inden-1-one (100 mg, 475 μmol) and cyclohexylamine (94 mg, 951 μmol) were dissolved in 2 mL of dry benzene and stirred under N2 until precipitation ceased (˜15 min). The cyclohexylamine•HBr was removed by filtration. The filtrate was applied to a flash SiO2 column that was developed with 8:1 hexanes-EtOAc to give the title compound as a clear oil (91 mg, 84% yield).

Workup

  1. custom(˜15 min)
  2. customThe cyclohexylamine•HBr was removed by filtration

Sources & evidence

ORD record
ord-44ffc9d453cf48b2b7756dc3c2501105
Source dataset
uspto-grants-2015_09
Patent number
US09127016B2

Reaction notes

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