Benzene, 1-chloro-4-fluoro- → HCID 131711661, compound

HRID 1447656Notes

Reaction equation

HRID 1447656 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:17])[C@@H:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[C@H:7]([OH:16])[CH2:6]1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](F)=[CH:21][CH:20]=1>CS(C)=O>[CH3:3][N:4]([CH3:17])[C@@H:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[C@H:7]([O:16][C:22]2[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 9604Benzene, 1-chloro-4-fluoro-HCID 24758Sodium hydrideHCID 86736721HCID 86736721, compound

Product 1

HCID 131711661HCID 131711661, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

0.6 ml of dimethylsulfoxide were added at room temperature to 60 mg of sodium hydride in a 50% oil dispersion and the mixture was heated to 50° C. for 20 minutes and was then cooled to 20° C. 205 mg of cis 7-dimethylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol were added thereto and after stirring the mixture for 15 minutes, 0.13 ml of p-chloro-fluorobenzene was added thereto. The mixture stood for one hour at 20° C. and was heated at 50° C. for 90 minutes and for 3 hours at 100° C. The mixture was cooled to 20° C. and was extracted with 30 ml of methylene chloride. The organic phase was washed with water, dried and evaporated to dryness to obtain 300 mg of raw product which was chromatographed over silica gel. Elution with a 7-3 chloroform-methanol mixture and evaporation of the solvent yielded 250 mg of cis N,N-dimethyl-5-[4-chlorophenoxy]-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-amine in the form of an oil.

Workup

  1. temperaturewas then cooled to 20° C
  2. waitThe mixture stood for one hour at 20° C.
  3. temperaturewas heated at 50° C. for 90 minutes and for 3 hours at 100° C
  4. temperatureThe mixture was cooled to 20° C.
  5. extractionwas extracted with 30 ml of methylene chloride
  6. washThe organic phase was washed with water
  7. customdried
  8. customevaporated to dryness
  9. customto obtain 300 mg of raw product which
  10. customwas chromatographed over silica gel
  11. washElution
  12. customwith a 7-3 chloroform-methanol mixture and evaporation of the solvent

Sources & evidence

ORD record
ord-77babc29d5704d47ac91e1890623876e
Source dataset
uspto-grants-1979_12
Patent number
US04177292

Reaction notes

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