Diisopropyl Ether → HCID 23362124, compound

HRID 1082089Notes

Reaction equation

HRID 1082089 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16](=O)[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[CH2:13][CH:14]=2)=[CH:5][CH:4]=1.[OH-].[Na+].[BH4-].[Na+].C([O:34]C(C)C)(C)C>CO>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[OH:34])[CH2:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 67770521HCID 67770521, compound

Product 1

HCID 23362124HCID 23362124, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After adding 12.93 g (0.03 mol) of 3-[4-(4-chlorophenyl)-1,2,3,6-tetrahydro-1-pyridyl]-1-(2,4-dichlorophenyl)propanone hydrochloride to a solution of 1.2 g (0.03 mol) of sodium hydroxide in 50 ml of methanol, 1.17 g of sodium borohydride are portionwise added to the above mixture over 1 hour. After terminating the addition, the reaction mixture is boiled under reflux for 3 hours, then the reaction mixture is poured into 150 ml of water. The major part of methanol is distilled off from the so-obtained oily precipitate, which is then twice extracted with 50 ml of ethyl acetate each. After evaporating the solvent, 12.3 g of evaporation residue are obtained to give a crystalline product on addition of 50 ml of diisopropyl ether. In this way 8.32 g of title product are obtained, which is recrystallized from 28 ml of isopropanol to obtain 6.3 g of title compound, m.p.: 96°-98° C.

Workup

  1. additionare portionwise added to the above mixture over 1 hour
  2. customAfter terminating
  3. additionthe addition
  4. temperatureunder reflux for 3 hours
  5. additionthe reaction mixture is poured into 150 ml of water
  6. distillationThe major part of methanol is distilled off from the so-obtained oily precipitate, which
  7. extractionis then twice extracted with 50 ml of ethyl acetate each
  8. customAfter evaporating
  9. customthe solvent, 12.3 g of evaporation residue
  10. customare obtained
  11. customto give a crystalline product

Sources & evidence

ORD record
ord-d665462eac6946ee8325c5035a5562c3
Source dataset
uspto-grants-1996_12
Patent number
US05589486

Reaction notes

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