Hydrochloric Acid → HCID 25018665, compound

HRID 1697444Notes

Reaction equation

HRID 1697444 reaction equation
[N:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([C:4]3=O)[CH2:2]1)[CH2:8]2.Cl.[CH2:13]([O:20][NH2:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>C(O)C>[CH2:13]([O:20][N:21]=[C:4]1[CH:5]2[CH2:10][N:1]3[CH2:8][CH:7]([CH2:9][CH:3]1[CH2:2]3)[CH2:6]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 102312Benzyloxyamine hydrochlorideHCID 1426421-Azatricyclo(3.3.1.1,3,7)decan-4-one

Product 1

HCID 25018665HCID 25018665, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-azatricyclo[3.3.1.13,7]decan-4-one (45 mg, 0.30 mmol) (prepared as reported in Becker, D. P. and Flynn, D. L. Synthesis 1992, 1080-1082) and O-benzylhydroxylamine hydrochloride (Aldrich, 51 mg, 0.32 mmol) were combined in a test tube with ethanol (3 mL). Concentrated hydrochloric acid (12 M, 0.1 mL) was added, and the mixture was heated at reflux until the solids dissolved. The solution was allowed to stand at room temperature overnight, then concentrated under vacuum. The residue was dissolved in acetonitrile (0.7 mL), and the solution was diluted with ethyl acetate (5 mL). The resulting white precipitate was collected by filtration, washed with ethyl acetate (2 mL) and dried under vacuum to provide the title compound as the hydrochloride salt. 1H NMR (300 MHz, CD3OD) δ 1.89-2.07 (m, 2 H), 2.15-2.37 (m, 3 H), 2.85 (s, 1 H), 3.42-3.85 (m, 7 H), 5.08 (s, 2 H), 7.24-7.40 ppm (m, 5 H); MS (DCI/NH3) m/z 257 (M+H)+; Anal. C16H20N2O-2HCl requires C, 58.36; H, 6.73; N, 8.51; Found C, 58.61; H, 6.49; N, 8.48.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux until the solids
  3. dissolutiondissolved
  4. concentrationconcentrated under vacuum
  5. dissolutionThe residue was dissolved in acetonitrile (0.7 mL)
  6. additionthe solution was diluted with ethyl acetate (5 mL)
  7. filtrationThe resulting white precipitate was collected by filtration
  8. washwashed with ethyl acetate (2 mL)
  9. customdried under vacuum

Sources & evidence

ORD record
ord-6280ce066a874a31b4cd5a837f6adca5
Source dataset
uspto-grants-2012_04
Patent number
US08163915B2

Reaction notes

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