4-Methylquinoline → HCID 68587788, compound

HRID 1773004Notes

Reaction equation

HRID 1773004 reaction equation
[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1.[BrH:12].[Br:13][CH2:14][CH2:15][CH2:16][NH2:17]>ClC1C=CC=CC=1Cl.CO>[Br-:13].[NH3+:17][CH2:16][CH2:15][CH2:14][N+:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1.[Br-:12]

Participants

5

Reactant 2

HCID 102854-MethylquinolineHCID 787013-Bromopropylamine hydrobromide

Product 1

HCID 68587788HCID 68587788, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of lepidine (3.0 g, 21 mmol) and 3-bromopropylamine hydrobromide (4.6 g, 21 mmol) in 1,2-dichlorobenzene (50 mL) was heated at 135° C. for 16 hours. The mixture was cooled and 1,2-dichlorobenzene was decanted. The residue thus obtained was suspended in methanol (25 mL) and refluxed for 10 min. It was cooled and separated solid was collected by centrifugation, washed with methanol (2×30 mL) and dried under high vacuum to yield Compound 2 as an light gray solid (1.4 g, 19%). This product was used without further purification. The structure of Compound 1 is given below:

Workup

  1. temperatureThe mixture was cooled
  2. custom1,2-dichlorobenzene was decanted
  3. customThe residue thus obtained
  4. temperaturerefluxed for 10 min
  5. temperatureIt was cooled
  6. customseparated solid
  7. customwas collected by centrifugation
  8. washwashed with methanol (2×30 mL)
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-29542f9d9b524a00b9253d81deee5d11
Source dataset
uspto-grants-2016_02
Patent number
US09250249B2

Reaction notes

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