Acetone → N-[2-(2,3,7,8-Tetrahydrofuro[2,3-g]indol-1-yl)ethyl]acetamide

HRID 1781324Notes

Reaction equation

HRID 1781324 reaction equation
[O:1]1[C:10]2[C:5](=[C:6]([NH2:11])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]C1.[I-].[K+].Cl[CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19].[CH3:21][C:22](C)=O>>[N:11]1([CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[C:6]2[C:7](=[CH:8][CH:9]=[C:10]3[O:1][CH2:3][CH2:4][C:5]3=2)[CH2:22][CH2:21]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 4875Potassium IodideHCID 81815N-(2-Chloroethyl)acetamideHCID 18739714HCID 18739714, compound

Product 1

HCID 5311134N-[2-(2,3,7,8-Tetrahydrofuro[2,3-g]indol-1-yl)ethyl]acetamide

Procedure

A mixture of Intermediate 4 (50 mg), potassium iodide (1 g) and N-(2-chloroethyl)acetamide (96 mg) in acetone (5 ml) was heated to reflux for 2 days. The cooled mixture was partitioned between water and ethyl acetate. The extracts were dried, and evaporated, and the residue chromatographed on silica gel. Elution with CH2Cl2 :EtOH:NH3 ; 400:8:1 gave a sample of desired material (69 mg).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 days
  3. customThe cooled mixture was partitioned between water and ethyl acetate
  4. customThe extracts were dried
  5. customevaporated
  6. customthe residue chromatographed on silica gel
  7. washElution with CH2Cl2

Sources & evidence

ORD record
ord-dd274f47e9044758accf665671201e6c
Source dataset
uspto-grants-1997_05
Patent number
US05633276

Reaction notes

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