Formamidine acetate → HCID 70926467, compound

HRID 1042395Notes

Reaction equation

HRID 1042395 reaction equation
[CH3:1][C:2]1([CH3:16])[C:10]2[CH2:9][CH:8]([CH3:11])[CH2:7][C:6](=O)[C:5]=2[C:4]([CH3:14])([CH3:13])[CH:3]1[CH3:15].[C:17](O)(=O)C.[CH:21]([NH2:23])=[NH:22]>C(O)CCC>[CH3:1][C:2]1([CH3:16])[C:10]2[C:9]3[C:8]([CH:7]([CH3:17])[CH2:6][C:5]=2[C:4]([CH3:14])([CH3:13])[CH:3]1[CH3:15])=[CH:11][N:23]=[CH:21][N:22]=3

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 70926808HCID 70926808, compound

Product 1

HCID 70926467HCID 70926467, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 1,1,2,3,3,6-hexamethyl-1,2,3,5,6,7-hexahydro-inden-4-one (prepared as described in U.S. Pat. No. 3,927,083) (10 g, 0.045 mol), formamidine acetate (23 g, 0.22 mol), and butanol (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 (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 1,1,2,3,3,5-hexamethyl-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 (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-afa3d65cfd5f43bfa02f8bdd1e6399b5
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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