Methyl iodide → Ethyl 1-(6-chloro-2-methyl-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)cyclobutanecarboxylate Hydrochloride

HRID 1700369Notes

Reaction equation

HRID 1700369 reaction equation
CI.[C:3]([O-])(O)=O.[Na+].Cl.[Cl:9][C:10]1[CH:11]=[C:12]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]1[CH:17]([C:23]3([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:26][CH2:25][CH2:24]3)[NH:16][CH2:15][CH2:14][C:13]2=1>C(O)C>[ClH:9].[Cl:9][C:10]1[CH:11]=[C:12]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]1[CH:17]([C:23]3([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:24][CH2:25][CH2:26]3)[N:16]([CH3:3])[CH2:15][CH2:14][C:13]2=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 18317933Ethyl 1-(6-chloro-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)cyclobutanecarboxylate Hydrochloride

Product 1

HCID 18317948Ethyl 1-(6-chloro-2-methyl-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)cyclobutanecarboxylate Hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.3 ml of methyl iodide and 0.8 g of NaHCO3 are added to a solution of 1 g of the compound of Example 1 in 25 ml of ethanol. After reaction for 24 hours at ambient temperature, the reaction mixture is concentrated under reduced pressure and then the residue is taken up in a mixture of water and dichloromethane. After extraction, drying and filtration, the organic phase is concentrated under reduced pressure. Crystallisation from a solution of ethanol and ethereal hydrogen chloride enables the expected product to be obtained.

Workup

  1. customAfter reaction for 24 hours at ambient temperature
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. additionthe residue is taken up in a mixture of water and dichloromethane
  4. extractionAfter extraction
  5. customdrying
  6. filtrationfiltration
  7. concentrationthe organic phase is concentrated under reduced pressure
  8. customCrystallisation from a solution of ethanol and ethereal hydrogen chloride
  9. customto be obtained

Sources & evidence

ORD record
ord-156ac2c7456a43eea2e0cedad0ca637f
Source dataset
uspto-grants-2002_02
Patent number
US06350757B1

Reaction notes

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