Hydrochloric Acid → HCID 18362759, compound

HRID 914999Notes

Reaction equation

HRID 914999 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1)=[O:3].[CH2:13]([CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.[CH2:27]=O>C(O)C.CCOC(C)=O>[CH2:13]([CH:20]1[CH2:25][CH2:24][N:23]([CH2:27][CH2:1][C:2]([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=2)=[O:3])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8494m-NitroacetophenoneHCID 317384-Benzylpiperidine

Product 1

HCID 18362759HCID 18362759, compoundYield 20.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-nitroacetophenone (109) (0.60 g, 3.63 mmol) and 4-benzylpiperidine (103) (0.64 g, 3.63 mmol) in absolute ethanol (5 mL) was added concentrated hydrochloric acid (0.30 mL, 3.60 mmol). The mixture was heated under reflux and paraformaldehyde (0.32 g, 10.96 mmol) was added in four portions over a period of 40 minutes. The resulting mixture was heated under reflux overnight before it was allowed to cool to room temperature and diluted with EtOAc (100 mL). Following sequential washings with 1 N NaOH (2×100 mL), water (100 mL), and brine (100 mL), the organic solution was dried (Na2SO4) and concentrated. The residue was purified via flash silica gel chromatography to provide 110 (0.26 g, 20%) as a dark syrup.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. temperatureThe resulting mixture was heated
  4. temperatureunder reflux overnight before it
  5. washwashings with 1 N NaOH (2×100 mL), water (100 mL), and brine (100 mL)
  6. dry with materialthe organic solution was dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified via flash silica gel chromatography

Sources & evidence

ORD record
ord-3adb16433d074972bf7db4c2b06ccaa3
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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