Chloride → HCID 22236436, compound

HRID 1744001Notes

Reaction equation

HRID 1744001 reaction equation
[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([OH:12])=[CH:4][CH:3]=1.Cl.[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17]Cl.C(=O)([O-])[O-].[K+].[K+].[Cl-]>C(#N)C>[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([O:12][CH2:17][CH2:16][N:15]([CH3:19])[CH3:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 222364764-Bromo-5,6,7,8-tetrahydronaphthalen-1-ol

Product 1

HCID 22236436HCID 22236436, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 1 L round-bottomed flask equipped with condenser and N2 inlet were added 10.0 g (44 mmol) 4-bromo-5,6,7,8-tetrahydro-naphthalen-1-ol (Example 37A), 19 g (130 mmol) 2-dimethylaminoethyl chloride hydrochloride, 30.3 g (220 mmol) powdered potassium carbonate, and 600 mL acetonitrile. The reaction was refluxed 60 hours, followed by an additional portion of the chloride and continued refluxing for 24 hours. The reaction was cooled, filtered and concentrated. The residue was chromatographed on silica gel using methanol/methylene chloride as eluant to afford 8.55 g (65%) of a light brown oil.

Workup

  1. customTo a 1 L round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 60 hours
  3. temperaturecontinued refluxing for 24 hours
  4. temperatureThe reaction was cooled
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-966f5e19683d4aa5b4a5704a027b5589
Source dataset
uspto-grants-2006_03
Patent number
US07012078B2

Reaction notes

Loading…