Isopropanol → HCID 14698740, compound

HRID 476929Notes

Reaction equation

HRID 476929 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[CH:3]=1.C(O[C:12]([CH:14]1[CH2:19][CH2:18][N:17]([C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])[CH2:16][CH2:15]1)=[O:13])C.[Cl-:27].[NH4+].[CH3:29][CH:30](O)[CH3:31].O1C[CH2:36][CH2:35][CH2:34]1>>[Cl:8][C:4]1[CH:5]=[CH:6][C:7]([C:12]([C:30]2[CH:31]=[CH:36][C:35]([Cl:27])=[CH:34][CH:29]=2)([OH:13])[CH:14]2[CH2:15][CH2:16][N:17]([C:20]([N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])=[O:21])[CH2:18][CH2:19]2)=[CH:2][CH:3]=1

Participants

6

Reactant 5

HCID 3776IsopropanolHCID 79281-Bromo-3-chlorobenzeneHCID 8028Tetrahydrofuran3×HCID 25517Ammonium ChlorideHCID 2989403HCID 2989403, compound

Product 1

HCID 14698740HCID 14698740, compound

Procedure

A Grignard solution was prepared by the treatment of a slurry of 8.5 g (0.35 mole) of mangesium chips in 200 ml of dry tetrahydrofuran (THF) with a solution of 72.8 g (0.38 mole) of 1-bromo-3-chlorobenzene in 400 ml of THF. After the addition was complete, the mixture was heated at reflux for 15 min to complete formation. To the Grignard solution at ambient temperature was added a solution of 38.4 g (0.15 mole) of 1-[(diethylamino)carbonyl]-4-piperidine carboxylic acid ethyl ester in 200 ml of THF in a stream. The solution was stirred at ambient temperature overnight and poured into 2.5 liters of a saturated ammonium chloride solution. The layers were separated and the aqueous layer was extracted once with 500 ml of methylene chloride and once with 250 ml of methylene chloride. The combined organic layers were filtered through Celite® and the filtrate was washed successively with 500 ml of water, 750 ml of a 4% sodium hydroxide solution, 250 ml of water and 250 ml of brine. The solution was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a gum which crystallized. The solid was triturated with petroleum ether (30°-60° C.), collected by filtration, and dried to yield 56.7 g (87,) of a white solid. An analytical sample, m.p. 172°-175° C. was prepared from 2-propanol.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 15 min
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted once with 500 ml of methylene chloride and once with 250 ml of methylene chloride
  6. filtrationThe combined organic layers were filtered through Celite®
  7. washthe filtrate was washed successively with 500 ml of water, 750 ml of a 4% sodium hydroxide solution, 250 ml of water and 250 ml of brine
  8. dry with materialThe solution was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customto give a gum which
  11. customcrystallized
  12. customThe solid was triturated with petroleum ether (30°-60° C.)
  13. filtrationcollected by filtration
  14. customdried
  15. customto yield 56.7 g (87,) of a white solid

Sources & evidence

ORD record
ord-0bc20f36759f473caedc5a1aeeef38a1
Source dataset
uspto-grants-1989_12
Patent number
US04886794

Reaction notes

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