Hydrochloric Acid → HCID 19823639, compound

HRID 728270Notes

Reaction equation

HRID 728270 reaction equation
[CH3:1][N:2]([CH3:20])[CH:3]([C:9]1([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)[C:4](=[O:8])[CH2:5][CH2:6][CH3:7].O.Cl>O1CCCC1>[CH3:20][N:2]([CH3:1])[CH:3]([C:9]1([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)[CH:4]([OH:8])[CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 19823614HCID 19823614, compound

Product 1

HCID 19823639HCID 19823639, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Boranedimethylsulphide complex (3 ml) was added dropwise under nitrogen over a period of 20 minutes to a solution of 1-dimethylamino-1-[1-(4-tolyl)cyclobutyl]pentan-2-one (1.85 g prepared as described in Example 16) in tetrahydrofuran (20 ml) and the resulting mixture stirred for 3 days at ambient temperature. The mixture was cooled to 0° C. and water (25 ml) and then 5N hydrochloric acid (25 ml) added. The mixture was basified and the tetrahydrofuran removed by evaporation. The residue was extracted with ether and the extracts washed with water, dried, filtered and evaporated to give an oil which was dissolved in petroleum ether (b.p. 80°-100° C.) and purified on a column packed with magnesia-silica gel sold under the trade name Florisil using petroleum ether (b.p. 80° to 100° C.) as eluant. The eluate was evaporated to give an oil which was distilled (215° C./1.5 mm Hg) to give 1-dimethylamino-1-[1 -(4-tolyl)cyclobutyl]pentan-2-ol.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customthe tetrahydrofuran removed by evaporation
  3. extractionThe residue was extracted with ether
  4. washthe extracts washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customto give an oil which
  9. custompurified on a column
  10. customThe eluate was evaporated
  11. customto give an oil which
  12. distillationwas distilled (215° C./1.5 mm Hg)

Sources & evidence

ORD record
ord-5743e3f593b042d2856ff6c0aebdd149
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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