Methyl iodide → HCID 70426537, compound

HRID 1906222Notes

Reaction equation

HRID 1906222 reaction equation
CI.[C:3]1([CH2:9][NH:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][C:23]([NH2:25])=[O:24])[CH:20]=3)[NH:15][CH:14]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:26](N(C(C)C)CC)(C)C>O1CCCC1>[OH2:24].[CH3:26][N:10]([CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH2:11][CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][C:23]([NH2:25])=[O:24])[CH:20]=2)[NH:15][CH:14]=1.[CH3:26][N:10]([CH2:11][CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][C:23]([NH2:25])=[O:24])[CH:20]=2)[NH:15][CH:14]=1)[CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 12805193HCID 12805193, compound

Product 1

HCID 70426537HCID 70426537, compoundYield 124%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl iodide (0.83 g) in tetrahydrofuran (50 ml) was added at room temperature to a solution of 3-[2-[(phenylmethyl)amino]ethyl]-1H-indole-5-acetamide (1.8 g) and diisopropylethylamine (0.76 g) in dry tetrahydrofuran (150 ml). The resulting solution was stirred at room temperature for 16 h and was then evaporated in vacuo to dryness. The residue was partitioned between chloroform (225 ml) and 8% aqueous sodium hydrogen carbonate (250 ml). The organic layer was run off and the aqueous layer extracted with more chloroform (200 ml). The combined organic solutions were dried (Na2SO4), filtered and evaporated to afford a gum (1.6 g) which was purified by column chromatography on silica gel (Merck Type 60, 250 g) eluting with methanol in chloroform (1-10%). The product-bearing fractions afforded the title compound as a pale yellow oil which slowly crystallised on standing 0.4 g m.p. 123°-126° (bubbles above 93°).

Workup

  1. customwas then evaporated in vacuo to dryness
  2. customThe residue was partitioned between chloroform (225 ml) and 8% aqueous sodium hydrogen carbonate (250 ml)
  3. extractionthe aqueous layer extracted with more chloroform (200 ml)
  4. dry with materialThe combined organic solutions were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c084af4ce91e4669b5f282508b052861
Source dataset
uspto-grants-1987_03
Patent number
US04650810

Reaction notes

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