Cycloheptylamine → N-Cycloheptyl-[(2-phenanthrenyl)methyl]amine

HRID 37640

Reaction equation

HRID 37640 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5][C:4]=2[CH:3]=1.BrN1C(=O)CCC1=O.[CH:24]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:24]1([NH:31][CH2:1][C:2]2[CH:15]=[CH:14][C:13]3[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH:6]=[CH:5][C:4]=3[CH:3]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 2899CycloheptylamineHCID 11430Potassium CarbonateHCID 173212-MethylphenanthreneHCID 67184N-bromobutanimide

Product 1

HCID 15284290N-Cycloheptyl-[(2-phenanthrenyl)methyl]amineYield 66.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methylphenanthrene (2.00 g, 10.4 mmol) was brominated with N-bromosuccinimide (2.05 g, 11.5 mmol) and the product compound was added gradually to a suspension of cycloheptylamine (2.38 g, 21.0 mmol) and potassium carbonate (2.90 μg, 21.0 mmol) in dimethylformamide (20 ml) with ice-cooling. The mixture was then stirred at room temperature for 16 hrs and, then, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 2.11 g of a viscous liquid. 1H-NMR (δ ppm, in deuteriochloroform) 2.83 (2H, m), 4.02 (2H, s), 8.68 (2H, m)

Workup

  1. temperaturecooling
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b2325b9e98944fdc89b7e22fd4005c14
Source dataset
uspto-grants-1995_05
Patent number
US05420348

Linked notes

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