Water → HCID 23464741, compound

HRID 444233Notes

Reaction equation

HRID 444233 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)=[C:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1.[H-].[Na+].[H][H].O.C1(C)[C:28]([CH3:33])=[CH:29][CH:30]=[CH:31]C=1>C1(Br)CCCC1>[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)=[C:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:33]2)[CH2:10][CH2:9]1

Participants

7

Reactant 5

HCID 962WaterHCID 7237O-Xylene2×HCID 24758Sodium hydrideHCID 23464739HCID 23464739, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23464741HCID 23464741, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8728BromocyclopentaneSolvent

Procedure

6 grams (0.0175 mole) of 4-(di-2-thienyl-methylene)-N-(2-hydroxyethyl)-piperidine hydrochloride were added in portions to a suspension of 1.3 grams of NaH (80%) in 100 ml of dry xylene. The mixture was heated to boiling until the evolution of hydrogen stopped. At the boiling heat there were dropped in 5.3 grams of cyclopentyl bromide dissolved in 10 ml of xylene. After 16 hours reaction time the product was hydrolyzed in the cold with water, the xylene phase separated off, dry and concentrated. The product was purified by chromatography using silica gel for the dry column chromatography employing ethyl acetate as elution agent and the oxalate precipitated from acetone solution. M.P. of the oxalate 193°-195° C.; Yield 32%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureAt the boiling heat there
  3. customAfter 16 hours reaction time the product
  4. customthe xylene phase separated off
  5. customdry
  6. concentrationconcentrated
  7. customThe product was purified by chromatography
  8. washas elution agent
  9. customthe oxalate precipitated from acetone solution
  10. customM.P. of the oxalate 193°-195° C.

Sources & evidence

ORD record
ord-4f3869adb59e4fc1bc0a5399bebcc2d5
Source dataset
uspto-grants-1981_04
Patent number
US04263308

Reaction notes

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