Formamidine acetate → HCID 70926371, compound

HRID 1042393Notes

Reaction equation

HRID 1042393 reaction equation
[CH3:1][C:2]1([CH3:14])[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=O)[C:5]=2[C:4]([CH3:13])([CH3:12])[CH2:3]1.[C:15](O)(=O)C.[CH:19]([NH2:21])=[NH:20]>C(O)CCC>[CH3:12][C:4]1([CH3:13])[C:5]2[C:6]3[C:7]([CH2:8][CH2:9][C:10]=2[C:2]([CH3:1])([CH3:14])[CH2:3]1)=[CH:15][N:21]=[CH:19][N:20]=3

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 86673205HCID 86673205, compound

Product 1

HCID 70926371HCID 70926371, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 1,1,3,3-tetramethyl-1,2,3,5,6,7-hexahydro-inden-4-one (prepared as described in U.S. Pat. No. 3,927,083) (10 g, 0.05 mol), formamidine acetate (27 g, 0.26 mol), and butanol (C4H9OH) (50 mL). The reaction mixture is heated to 130° C. and stirred for 24 hours. The crude mass is washed once with aqueous sulfuric acid (H2SO4) (10%, 100 mL) followed by twice with brine (30 mL). Butanol is recovered by roto-evaporation. The crude product is further purified with liquid chromatography (Biotage® system) and then crystallized. Product 1,1,3,3-tetramethyl-2,3,4,5-tetrahydro-1H-7,9-diaza-cyclopenta[a]naphthalene (˜5 g) is obtained.

Workup

  1. customA 100 mL reaction flask
  2. customprepared
  3. washThe crude mass is washed once with aqueous sulfuric acid (H2SO4) (10%, 100 mL)
  4. customButanol is recovered by roto-evaporation
  5. customThe crude product is further purified with liquid chromatography (Biotage® system)
  6. customcrystallized

Sources & evidence

ORD record
ord-aab87e3d06d84b559c3f34cff4e49514
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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