Hydrochloric Acid → HCID 20058541, compound

HRID 2050568Notes

Reaction equation

HRID 2050568 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH:8]([NH2:16])[CH2:9]2.[C:17](=[O:20])([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br.Cl>C(#N)C>[ClH:1].[ClH:1].[CH3:2][O:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH:8]([NH:16][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:16][CH:8]1[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][CH:12]=[C:13]([O:20][CH3:17])[C:4]=3[O:3][CH3:2])[CH2:9]1)[CH2:9]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 123815925,6-Dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine--hydrogen chloride (1/1)

Product 1

HCID 20058541HCID 20058541, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

1,2,3,4-Tetrahydro-5,6-dimethoxy-2-naphthalenamine hydrochloride (4.87 g) in acetonitrile (100 ml) was added slowly to a stirred suspension of potassium carbonate (3.0 g) in a refluxing solution of 1,6-dibromohexane (2.44 g) in acetonitrile (100 ml) over a period of 1 hour. When the addition was complete, reflux was continued for 24 hours, the solution filtered to remove inorganic salts, and the filtrate evaporated in vacuo to give an oil. Chromatography on silica, eluting with chloroform: methanol 95:5 , gave, following trituration with ethereal hydrogen chloride, the title compound 1.15 g (20%), mp 275° (decomp)

Workup

  1. additionWhen the addition
  2. temperaturereflux
  3. filtrationthe solution filtered
  4. customto remove inorganic salts
  5. customthe filtrate evaporated in vacuo
  6. customto give an oil
  7. washChromatography on silica, eluting with chloroform: methanol 95:5
  8. customgave

Sources & evidence

ORD record
ord-6013835f86d540539715531c802dba57
Source dataset
uspto-grants-1991_05
Patent number
US05013760

Reaction notes

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