Hydrochloric Acid → 197144-89-1

HRID 2394980Notes

Reaction equation

HRID 2394980 reaction equation
C[O:2][C:3]1[CH:4]=[C:5](/[C:9](=[CH:16]\[CH3:17])/[CH:10]([CH3:15])[CH2:11][N:12]([CH3:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1.[H-].C([Al+]CC(C)C)C(C)C.C(O)C.[ClH:31]>C1(C)C=CC=CC=1.CC(C)=O.C(O)C.O>[ClH:31].[CH3:14][N:12]([CH3:13])[CH2:11][CH:10](/[C:9](/[C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=1)=[CH:16]/[CH3:17])[CH3:15]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 15837912HCID 15837912, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 131720841197144-89-1

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1140TolueneSolvent3×HCID 19096565Water ethanolSolvent

Conditions

Temperature
0 °C

Procedure

182 g (Z)-(RS)-[3-(3-methoxy-phenyl)-2-methyl-pent-3-enyl]-dimethylamine, dissolved in 360 ml toluene, were added drop-wise at room temperature to 1.6 l of a 20 weight % solution of diisobutylaluminium hydride in toluene. The mixture was then heated for 11 hours under reflux. After cooling to 0° C., 450 ml ethanol were added drop-wise with cooling. The mixture was then stirred for 15 minutes and diluted with 1 l toluene. Thereafter, 450 ml of an ethanol/water mixture (1:1) were added drop-wise with cooling. After stirring for one hour at room temperature, the precipitated aluminium hydroxide was filtered off under suction and the solvent was removed from the organic phase by distillation. 167 g (97.6% theoretical) of crude base were obtained, which were dissolved in 1.67 l acetone and treated with 65 ml of concentrated hydrochloric acid. 152 g (76% theoretical) of hydrochloride (3) crystallised out, and had a melting point of 161°-162° C.

Workup

  1. temperatureThe mixture was then heated for 11 hours
  2. temperatureunder reflux
  3. temperaturewith cooling
  4. temperaturewith cooling
  5. stirringAfter stirring for one hour at room temperature
  6. filtrationthe precipitated aluminium hydroxide was filtered off under suction
  7. customthe solvent was removed from the organic phase by distillation
  8. custom167 g (97.6% theoretical) of crude base were obtained
  9. custom152 g (76% theoretical) of hydrochloride (3) crystallised out

Sources & evidence

ORD record
ord-3ca3d00d4f2d4a59bb04828d03107585
Source dataset
uspto-grants-1998_09
Patent number
US05811582

Reaction notes

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