Sulfuric Acid → HCID 19356151, compound

HRID 377598Notes

Reaction equation

HRID 377598 reaction equation
[CH2:1]([CH2:8][NH:9][CH2:10][CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:14]=1)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.S(=O)(=O)(O)O.[OH-].[Na+].Cl[CH2:32]Cl>>[CH3:32][N:9]1[CH2:10][CH:11]([C:13]2[CH:14]=[C:15]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:16]=[CH:17][CH:18]=2)[C:2]2[C:1](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:8]1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6344Dichloromethane2×HCID 14798Sodium HydroxideHCID 19356191HCID 19356191, compound

Product 1

HCID 19356151HCID 19356151, compound

Procedure

1.5 g (4.8 mmol) of 2-benzylmethylamino-l-(3-methoxycarbonylmethylphenyl)ethanol are dissolved in 13 ml of dichloromethane. 3.7 ml of conc. sulfuric acid are added dropwise to this solution with cooling and stirring. It is stirred at room temperature for three hours. The reaction solution is diluted with dichloromethane and treated with ice. This solution is then adjusted to an alkaline pH using NaOH solution. The deposited organic phase is separated off. The aqueous phase is extracted twice more with dichloromethane. The combined organic phases are dried and the solvent is distilled off. The residue is taken up in ether and the solution is filtered. Methyl 3-[2-methyl-1,2,3,4-tetrahydro-4-(R,S)-isoquinolinyl]phenyl-acetate is obtained as an oil.

Workup

  1. temperaturewith cooling
  2. stirringIt is stirred at room temperature for three hours
  3. additiontreated with ice
  4. customThe deposited organic phase is separated off
  5. extractionThe aqueous phase is extracted twice more with dichloromethane
  6. customThe combined organic phases are dried
  7. distillationthe solvent is distilled off
  8. filtrationthe solution is filtered

Sources & evidence

ORD record
ord-95eb4749eaa140dea11593fa520a0d3f
Source dataset
uspto-grants-2000_02
Patent number
US06028080

Reaction notes

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