Diethyl Ether → HCID 22118897, compound

HRID 1275008Notes

Reaction equation

HRID 1275008 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:14][N:15]([CH2:19][CH2:20]Cl)[CH2:16][CH2:17]Cl.Cl.C(=O)([O-])[O-].[K+].[K+].CCOCC>C(O)CCC>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N:13]3[CH2:20][CH2:19][N:15]([CH3:14])[CH2:16][CH2:17]3)[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 5935Nitrogen mustard hydrochloride2×HCID 11430Potassium Carbonate2×HCID 2585641-Acetyl-6-aminoindoline

Product 1

HCID 22118897HCID 22118897, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A stirred mixture of 1-acetyl-6-amino-2,3-dihydro-1H-indole (D10, 37.8 g, 0.22 mole), mechlorethamine hydrochloride (46 g, 0.24 mole) and anhydrous potassium carbonate (80 g, 0.58 mole) in 1-butanol (1800 ml) was heated at reflux for 8 h, then additional mechlorethamine hydrochloride (25 g, 0.13 mole) and potassium carbonate (41 g, 0.30 mole) were added and reflux continued for 3 h. The reaction mixture was allowed to cool and then washed with water (1000 ml). The aqueous wash was extracted with ethyl acetate, and the extract combined with the 1-butanol solution and concentrated in vacuo. The brown oily residue (60 g) was chromatographed on silica gel eluting with 0-8% MeOH/DCM to give an orange oil, which was trituated with ether to afford the title compound as a beige solid (12.2 g, 22%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 h
  3. temperaturereflux
  4. temperatureto cool
  5. washwashed with water (1000 ml)
  6. washThe aqueous wash
  7. extractionwas extracted with ethyl acetate
  8. concentrationconcentrated in vacuo
  9. customThe brown oily residue (60 g) was chromatographed on silica gel eluting with 0-8% MeOH/DCM
  10. customto give an orange oil, which

Sources & evidence

ORD record
ord-5ca54176b2bc44b1ae9710bffdc3b2b9
Source dataset
uspto-grants-2000_12
Patent number
US06159979

Reaction notes

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