Hydrochloric Acid → HCID 58079414, compound

HRID 1521464

Reaction equation

HRID 1521464 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:10])N)[CH:5]=[CH:6][CH:7]=1.[N:11]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C:14](=O)[CH2:13][CH2:12]2.Cl>C(O)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:13]3[CH2:12][N:11]4[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]4)[C:14]=3[N:8]([CH3:10])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 64203071-Azabicyclo[3.2.2]nonan-4-oneHCID 53401181HCID 53401181, compound

Product 1

HCID 58079414HCID 58079414, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-(3-Bromophenyl)-1-methylhydrazine (0.50 g, 2.5 mmol) and 1-azabicyclo[3.2.2]nonan-4-one (0.38 g, 2.7 mmol) were dissolved in isopropanol (4 mL), and concentrated aqueous HCl (0.8 mL) was added. The reaction mixture was heated to reflux for 18 h, concentrated and basified using 2 N NaOH. The aqueous layer was extracted with methylene chloride (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by flash column chromatography (silica gel, 0%-100% solvent mixture B in methylene chloride; solvent mixture B=80:18:2 methylene chloride/methanol/concentrated ammonium hydroxide) to give the title compound (438 mg, 58%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 7.40 (d, J=2.0 Hz, 1H), 7.23 (d, J=8.4 Hz, 1H), 7.16 (d, J=1.6 Hz, 1H), 4.25 (s, 2H), 3.61 (s, 3H), 3.30-3.24 (m, 3H), 3.14-3.08 (m, 2H), 2.02-1.99 (m, 4H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. concentrationconcentrated
  4. extractionThe aqueous layer was extracted with methylene chloride (3×)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by flash column chromatography (silica gel, 0%-100% solvent mixture B in methylene chloride; solvent mixture B=80:18:2 methylene chloride/methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-9dc1c232c2a24b8aa8507b1e3ac59762
Source dataset
uspto-grants-2015_07
Patent number
US09073925B2

Linked notes

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