Potassium Iodide → HCID 12997499, compound

HRID 1760043Notes

Reaction equation

HRID 1760043 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[I-].[K+].Cl.[NH2:18][CH:19]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:20]([N:22]1[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][C:26]([O:34][CH3:35])=[C:27]([O:32][CH3:33])[CH:28]=2)[CH2:23]1)=[O:21]>C(OCC)(=O)C.CCCCCC.CN(C=O)C>[CH2:7]([NH:18][CH:19]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:20]([N:22]1[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][C:26]([O:34][CH3:35])=[C:27]([O:32][CH3:33])[CH:28]=2)[CH2:23]1)=[O:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 22599906HCID 22599906, compound

Product 1

HCID 12997499HCID 12997499, compoundYield 59.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Anhydrous potassium carbonate (120 mg), benzyl chloride (20 μl, 0.174 mmol) and a catalytic amount of potassium iodide were added to a DMF (1 ml) solution of N(2-amino-3,3-dimethylbutyryl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (43.2 mg, 0.141 mmol) obtained in Reference example 7, and the mixture was stirred at room temperature for 2 hours. The reaction solution was diluted with a 1:1 mixture (50 ml) of ethyl acetate and hexane, and washed with water. The organic layer was dried over anhydrous magnesium sulfate, the insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography using ethyl acetate and hexane (2:1) as an eluent to obtain the captioned compound (33.5 mg, 59.6%) as a colorless foamy substance.

Workup

  1. customobtained in Reference example 7
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationthe insoluble matter was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-248fac11a67647b7b7c5ac1c716a2399
Source dataset
uspto-grants-2005_01
Patent number
US06838465B2

Reaction notes

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