Hydrazine hydrate (1:1) → HCID 71114848, compound

HRID 1624043Notes

Reaction equation

HRID 1624043 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][C:11](=O)[C:10]([CH3:15])([CH3:14])[CH2:9]2)=[CH:4][CH:3]=1.C(OC([N:25]([CH3:27])C)N(C)C)(C)(C)C.O.[NH2:29]N>C(O)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12]3[CH:27]=[N:25][NH:29][C:11]=3[C:10]([CH3:15])([CH3:14])[CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 86674928HCID 86674928, compound

Product 1

HCID 71114848HCID 71114848, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

(+/−)-4-(4-Chlorophenyl)-2,2-dimethyl-cyclopentanone (0.250 g, 1.12 mmol) is dissolved in isopropanol (5 mL) and stirred. tert-Butoxybis(dimethylamino)methane (0.33 mL, 1.57 mmol) is added drop wise to the reaction. The reaction is heated in a sealed vial at 100° C. for 12 hours, cooled to room temperature, and concentrated to dryness. The residue is diluted with isopropanol (5 mL). Hydrazine hydrate (0.11 mL, 2.25 mmol) is added to the reaction and heated to 100° C. in a sealed vial for 5 hours. The reaction is concentrated in vacuo. The residue is purified by silica gel flash chromatography eluting with 20% ethyl acetate in hexanes to obtain the title compound (0.035 g, 13%) as a yellow film. ES/MS (m/z) 247.0 (M+1).

Workup

  1. customwise to the reaction
  2. temperaturecooled to room temperature
  3. concentrationconcentrated to dryness
  4. additionThe residue is diluted with isopropanol (5 mL)
  5. temperatureheated to 100° C. in a sealed vial for 5 hours
  6. concentrationThe reaction is concentrated in vacuo
  7. customThe residue is purified by silica gel flash chromatography
  8. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-766c443783a540ae9cc3c68a540cae69
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

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