Water → HCID 11528838, compound

HRID 1836617Notes

Reaction equation

HRID 1836617 reaction equation
O.[OH-].[Na+].[C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11](S(C1C=CC(C)=CC=1)(=O)=O)[CH:10]=[C:9]2[C@H:25]1[CH2:27][C@H:26]1[CH2:28][N:29]([CH3:31])[CH3:30])#[N:5]>C(O)C>[C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[C@H:25]1[CH2:27][C@H:26]1[CH2:28][N:29]([CH3:31])[CH3:30])#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 23518920HCID 23518920, compound

Product 1

HCID 11528838HCID 11528838, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Water (4 ml) and an aqueous solution of sodium hydroxide (2 ml, 10 N) were sequentially added to a flask charged with a solution of crude cis-2-[5-cyano-1-(p-toluenesulfonyl)indol-3-yl]-1-(N,N-dimethylaminomethyl)cyclo-propane dissolved in anhydrous ethanol (15 ml). The resulting mixture was heated at 70° C. for 1 h. The solvent was evaporated and the residue was taken up in brine (10 ml). The aqueous layer was extracted with 10% methanol/ethyl acetate (3×5 ml). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude material was purified by silica gel column chromatography and eluted using a step gradient of a solvent mixture [chloroform/(2 M ammonia/methanol), 90/10, 80/20]. The cis-2-[5-cyanoindol-3-yl]-1-(N,N-dimethylaminomethyl)cyclopropane was obtained as a white solid (63 mg, 75% yield over 3 steps): 1H NMR (400 MHz, CDCl3): δ8.47 (1H, br s), 8.07 (1H, s), 7.41 (2H, apparent q, J=8.0 Hz), 7.03 (1H, s), 2.37 (1H, dd, J=12.6, 4.7 Hz), 2.18 (6H, s), 1.97 (1H, m), 1.69 (1H, dd, J=12.6, 8.6 Hz), 1.34 (1H, m), 1.22 (1H, m), 0.71 (1H, q, J=5.0 Hz); MS m/e 240 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. extractionThe aqueous layer was extracted with 10% methanol/ethyl acetate (3×5 ml)
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by silica gel column chromatography
  6. washeluted

Sources & evidence

ORD record
ord-3dbf84dbca80490a9f3762c0365c4faf
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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