Dimethyl-(5-vinyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-yl)amine → (5-Ethyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-yl)dimethylamine

HRID 25336Notes

Reaction equation

HRID 25336 reaction equation
[CH3:1][N:2]([CH3:18])[CH:3]1[C:12]2[CH2:11][O:10][C:9]([CH:13]=[CH2:14])=[CH:8][C:7]3=[CH:15][NH:16][CH:17]=[C:5]([C:6]=23)[CH2:4]1>CO.[H][H].[Pd]>[CH2:13]([C:9]1[O:10][CH2:11][C:12]2[CH:3]([N:2]([CH3:1])[CH3:18])[CH2:4][C:5]3=[CH:17][NH:16][CH:15]=[C:7]([C:6]=23)[CH:8]=1)[CH3:14]

Participants

5

Reactant 1

HCID 69736453Dimethyl-(5-vinyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-yl)amine

Product 1

HCID 69737167(5-Ethyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-yl)dimethylamineYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

Compound (40) 242 mg was dissolved in methanol 4 ml and 5% palladium/C 60 mg was added. A mixture was stirred in hydrogen atmosphere at room temperature for 3 h. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue obtained was chromatographed on aluminum oxide in ethyl acetate:hexane (1:2) to give the titled compound as colorless crystals 241.6 mg. Yield 99%. This was recrystallized from acetone-hexane to give the titled compound as colorless crystals, m.p. 91-92° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue obtained
  4. customwas chromatographed on aluminum oxide in ethyl acetate:hexane (1:2)

Sources & evidence

ORD record
ord-da8661081381406dbab38b6ee040d84d
Source dataset
uspto-grants-2005_02
Patent number
US06858640B2

Reaction notes

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