Water → HCID 68719328, compound

HRID 2383025Notes

Reaction equation

HRID 2383025 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].Cl.[CH:8]([CH:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[CH2:14][CH2:13][NH:12]1)([CH3:10])[CH3:9].[OH2:23]>>[C:1]([OH:2])(=[O:4])[CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[OH:23].[CH:8]([CH:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[CH2:14][CH2:13][NH:12]1)([CH3:10])[CH3:9]

Participants

4

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 53492926HCID 53492926, compound

Product 1

HCID 68719328HCID 68719328, compound

Conditions

Temperature
95 °C

Procedure

Potassium carbonate (92 g) and water (500 mL) were added to 1-isopropyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (86 g). The reaction mixture was extracted with EtOAc and dried over magnesium sulfate, and then the solvent was evaporated. To the resulting residue were added iPrOH (1100 mL) and (+)-mandelic acid (50 g), followed by stirring under heating at 95° C. for dissolution. The mixture was left to cool and stirred at room temperature overnight. The resulting solid was collected and repeatedly recrystallized three times using iPrOH to obtain 1-isopropyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline (+)-mandelate (43 g) as a single enantiomer.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent was evaporated
  4. additionTo the resulting residue were added iPrOH (1100 mL) and (+)-mandelic acid (50 g)
  5. waitThe mixture was left
  6. temperatureto cool
  7. stirringstirred at room temperature overnight
  8. customThe resulting solid was collected
  9. customrepeatedly recrystallized three times

Sources & evidence

ORD record
ord-a64c59662618425ea9b68c4ac8b53a82
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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