2,6-Lutidine → HCID 22132551, compound

HRID 1856786Notes

Reaction equation

HRID 1856786 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]3[C:20](=[O:21])[C:19]4=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]4[C:17]3=[O:26])[CH2:9]2)=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>ClCCl>[CH3:35][S:36]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]3[C:20](=[O:21])[C:19]4=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]4[C:17]3=[O:26])[CH2:9]2)=[CH:4][CH:3]=1)(=[O:38])=[O:37]

Participants

5

Reactant 3

HCID 79372,6-Lutidine2×HCID 31297Methanesulfonyl chloride2×HCID 22132546HCID 22132546, compound

Product 1

HCID 22132551HCID 22132551, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Amino-2-(4-phthalimidobutyl)-1,2,3,4-tetrahydroisoquinoline (3 g, 8.6 mmol) was dissolved in dichloromethane (100 ml), and 2,6-lutidine (1.2 ml, 10.32 mmol) was added. To this methylsulfonyl chloride (0.73 ml, 9.46 mmol) was added dropwise. A further portion of 2,6-lutidine (0.6 ml, 5.16 mmol) and methylsulfonyl chloride (0.37 ml, 4.78 mmol) were later added. The mixture was partitioned between sodium bicarbonate solution (100 ml) and dichloromethane (3×50 ml). The combined extracts were dried (Na2SO4) and evaporated in vacuo. Chromatography of the residue on alumina with ethyl acetate +0-1% methanol gradient elution gave the title compound as an oil (1.8 g, 49%).

Workup

  1. customThe mixture was partitioned between sodium bicarbonate solution (100 ml) and dichloromethane (3×50 ml)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. customevaporated in vacuo
  4. washChromatography of the residue on alumina with ethyl acetate +0-1% methanol gradient elution

Sources & evidence

ORD record
ord-1267c068a33a46aa97d19730c924a094
Source dataset
uspto-grants-2000_11
Patent number
US06143762

Reaction notes

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