Acetone → HCID 53998669, compound

HRID 1381551Notes

Reaction equation

HRID 1381551 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]([NH2:16])=[O:15])[CH:11]=2)[NH:6][CH:5]=1.[CH3:17][C:18]([CH3:20])=O.[BH3-]C#N.[Na+]>CO>[CH3:17][CH2:18][CH2:20][NH:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]([NH2:16])=[O:15])[CH:11]=2)[NH:6][CH:5]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 12803181HCID 12803181, compound

Product 1

HCID 53998669HCID 53998669, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.0 g (0.014 mole) of N-[3-(2-aminoethyl)-1H-indol-5-yl]urea, Example 1, in 100 ml MeOH was treated with 1.11 ml of acetone followed by 1.32 g (0.021 mole) of NaBH3CN and stirred for 18 hours. The solvent was removed in vacuo and the residue carefully dissolved in 20 ml of 20% HCl, heated for 15 minutes, cooled and neutralized with 4N NaOH to pH=12. The precipitated oil was extracted into EtOAc, dried over MgSO4, filtered and evaporated to give a glassy white solid. This material was purified by column chromatography (0.75% NH4OH/MeOH on silica gel) followed by recrystallization from acetone to give desired product: m.p. 145.5°-147°.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue carefully dissolved in 20 ml of 20% HCl
  3. temperatureheated for 15 minutes
  4. temperaturecooled
  5. extractionThe precipitated oil was extracted into EtOAc
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give a glassy white solid
  10. customThis material was purified by column chromatography (0.75% NH4OH/MeOH on silica gel)
  11. customfollowed by recrystallization from acetone

Sources & evidence

ORD record
ord-1bf0eba9c2cd43d3a07eb6eb8f228594
Source dataset
uspto-grants-1989_02
Patent number
US04803218

Reaction notes

Loading…