Indole → HCID 18656668, compound

HRID 55349Notes

Reaction equation

HRID 55349 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:15]=[CH:14][C:13]3[NH:12][CH2:11][C@@H:10]4[CH2:16][C@H:17]([N:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])[CH2:18][C:8]=2[C:9]=34)[CH:2]=1.N1C2C(=CC=CC=2)C=C1.C1([Se](O[Se](C2C=CC=CC=2)=O)=O)C=CC=CC=1>C1COCC1.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:15]=[CH:14][C:13]3[NH:12][CH:11]=[C:10]4[CH2:16][C@H:17]([N:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])[CH2:18][C:8]=2[C:9]=34)[CH:2]=1

Participants

6

Reactant 3

HCID 798IndoleHCID 87253Phenylseleninyl benzeneseleninateHCID 56979168HCID 56979168, compound

Product 1

HCID 18656668HCID 18656668, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.0 g (2.99 mmol) of (2aR,4S)-6-(3-pyridyl)-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole and 1.0 g (9 mmol) of indole in 50 ml of THF was treated at 0° C. with 0.61 g (1.70 mmol) of benzeneseleninic anhydride. The resulting solution was allowed to warm to room temperature. After 2 hours the reaction solution was diluted with water and the product was extracted into methylene chloride. The methylene chloride was evaporated and the resulting residue was taken up in aqueous tartaric acid. This acidic solution was washed with methylene chloride, then basified with 5M sodium hydroxide solution. The product was extracted into methylene chloride. After evaporating the methylene chloride the product was chromatographed over 25 g of silica gel using 10% ethyl acetate in toluene followed by 1:1 ethyl acetate/toluene as eluent. The material from the column was crystallized from toluene/hexane to afford 0.53 g of title compound.

Workup

  1. extractionthe product was extracted into methylene chloride
  2. customThe methylene chloride was evaporated
  3. washThis acidic solution was washed with methylene chloride
  4. extractionThe product was extracted into methylene chloride
  5. customAfter evaporating the methylene chloride the product
  6. customwas chromatographed over 25 g of silica gel using 10% ethyl acetate in toluene
  7. customThe material from the column was crystallized from toluene/hexane

Sources & evidence

ORD record
ord-1765eac9a4af4464a467710e9cd7519b
Source dataset
uspto-grants-1997_04
Patent number
US05624944

Reaction notes

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