Formamidine acetate → HCID 70926546, compound

HRID 1042398Notes

Reaction equation

HRID 1042398 reaction equation
[CH3:1][CH:2]1[CH2:11][CH:10]2[CH:5]([C:6]([CH3:16])([CH3:15])[CH2:7][CH:8]([CH3:14])[C:9]2([CH3:13])[CH3:12])[C:4](=O)[CH2:3]1.CC1CC2C(C)(C)C(C)CC(C)(C)C=2C(=O)C1.[H][H].[C:37](O)(=O)C.[CH:41]([NH2:43])=[NH:42]>[Pd].C(O)CCC>[CH3:1][CH:2]1[CH2:11][CH:10]2[C:9]([CH3:13])([CH3:12])[CH:8]([CH3:14])[CH2:7][C:6]([CH3:16])([CH3:15])[CH:5]2[C:4]2[N:43]=[CH:41][N:42]=[CH:37][C:3]1=2

Participants

7

Reactant 4

HCID 160693Formamidine acetateHCID 70926587HCID 70926587, compound2×HCID 70926989HCID 70926989, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70926546HCID 70926546, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

3,5,5,6,8,8-Hexamethyl-octahydro-naphthalen-1-one is first prepared by hydrogenating 3,5,5,6,8,8-hexamethyl-3,4,5,6,7,8-hexahydro-2H-naphthalen-1-one (prepared as described in U.S. Pat. No. 3,927,083) with Pd/C in alcohol in a Parr Hydrogenator at 25-60° C. and under 500 psi of hydrogen gas. A 100 mL reaction flask is the charged with 3,5,5,6,8,8-hexamethyl-octahydro-naphthalen-1-one (10 g, 0.042 mol), formamidine acetate (21 g, 0.2 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 5,7,7,8,10,10-hexamethyl-5,6,6a,7,8,9,10,10a-octahydro-benzo[h]quinazoline (˜5 g) is obtained.

Workup

  1. customprepared
  2. customat 25-60° C.
  3. customA 100 mL reaction flask
  4. washThe crude mass is washed once with aqueous sulfuric acid (10%, 100 mL)
  5. customButanol is recovered by roto-evaporation
  6. customThe crude product is further purified with liquid chromatography (Biotage® system)
  7. customcrystallized

Sources & evidence

ORD record
ord-e614247875524fd3b085cb991ab981f1
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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