Hydrochloric Acid → 4-[Benzyl(methyl)amino]cyclohexan-1-one

HRID 1193363Notes

Reaction equation

HRID 1193363 reaction equation
[CH2:1]([N:8]([CH3:19])[CH:9]1[CH2:18][CH2:17][C:12]2(OCC[O:13]2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([N:8]([CH3:19])[CH:9]1[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22009899N-Benzyl-N-methyl-1,4-dioxaspiro[4.5]decan-8-amine

Product 1

HCID 220099204-[Benzyl(methyl)amino]cyclohexan-1-oneYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Benzyl-N-methyl-1,4-dioxaspiro[4.5]decan-8-amine (1.0 g, 3.83 mmol, 1.0 eq.) was dissolved in MeOH (12 ml); 6 M HCl solution (12 ml) was added at 0° C., and stirring was carried out for 16 hours at RT. After monitoring by TLC, the solvent was removed under reduced pressure and the residue was taken up in water (50 ml), adjusted to pH 8-9 with NaCHO3 (solid) and extracted with DCM (2×50 ml). The combined org. phases were washed with water and sat. NaCl solution (in each case 50 ml), dried over sodium sulfate and concentrated under reduced pressure and dried. The crude product was used in the next stage without being purified further. Yield: 74% (620 mg, 2.857 mmol)

Workup

  1. customthe solvent was removed under reduced pressure
  2. extractionextracted with DCM (2×50 ml)
  3. washphases were washed with water and sat. NaCl solution (in each case 50 ml),
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customdried
  7. customwithout being purified further

Sources & evidence

ORD record
ord-9c194481ee3d499a88aa07cf168c1c07
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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