Pyridine → HCID 67082493, compound

HRID 1943555Notes

Reaction equation

HRID 1943555 reaction equation
O[CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]2([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:21]=3[F:27])[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1.N1C=CC=CC=1.S(Cl)([Cl:36])=O>C1(C)C=CC=CC=1.O>[Cl:36][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]2([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:21]=3[F:27])[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 67082406HCID 67082406, compound

Product 1

HCID 67082493HCID 67082493, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
45 °C

Procedure

The compound (41) (7.4 g), toluene (100 ml) and pyridine (0.5 ml) were put in a reaction vessel under a nitrogen atmosphere, and the mixture was stirred at 45° C. for 1 hour. Then, thionyl chloride (1.7 ml) was added in the temperature range of 45° C. to 55° C., and the mixture was heated under reflux for 2 hours. The reaction mixture was cooled to 25° C., and then poured into water (200 ml) and toluene (200 ml), and mixed. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and extraction into an organic phase was carried out. The organic phase obtained was fractionated, washed sequentially with a saturated aqueous solution of sodium hydrogencarbonate twice and with water three times, and then dried over anhydrous magnesium sulfate. The solution obtained was concentrated under reduced pressure, and the residue obtained was purified with a fractional operation by means of column chromatography using heptane as the eluent and silica gel as the stationary phase powder, and dried, giving 7.3 g of 4-chloromethyl-[4-pentyl-(2,3-difluorophenyl)cyclohexyl]-cyclohexane (42). The yield based on the compound (41) was 94.1%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction mixture was cooled to 25° C.
  4. additionmixed
  5. customhad separated into two phases of organic and
  6. extractionaqueous phases, and extraction into an organic phase
  7. customThe organic phase obtained
  8. washwashed sequentially with a saturated aqueous solution of sodium hydrogencarbonate twice
  9. dry with materialwith water three times, and then dried over anhydrous magnesium sulfate
  10. customThe solution obtained
  11. concentrationwas concentrated under reduced pressure
  12. customthe residue obtained
  13. customwas purified with a fractional operation by means of column chromatography
  14. customdried

Sources & evidence

ORD record
ord-a629ab3a03b34456879bb9acefde92a5
Source dataset
uspto-grants-2013_03
Patent number
US08394294B2

Reaction notes

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