Acetic Acid → HCID 86722615, compound

HRID 2271502Notes

Reaction equation

HRID 2271502 reaction equation
[CH2:1]([N:3]([CH2:6]C)[CH2:4][CH3:5])C.Cl.[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[CH:19]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)C1CNC1.C=O.C(O)(=O)C.[BH4-].C(O)(=O)C.[Na+].[OH-].[Na+]>CO>[CH3:6][N:3]1[CH2:1][CH:5]([CH:19]([C:10]2[CH:11]=[CH:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]=2)[O:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:4]1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 70676475HCID 70676475, compoundHCID 131733375HCID 131733375, compound

Product 1

HCID 86722615HCID 86722615, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (0.2 mL, 1.4 mmol) was added to 3-(naphthalen-2-yl(phenoxy)methyl)azetidine hydrochloride (0.3 g, 0.92 mmol) dissolved in the methanol solution (20 mL), and stirred at room temperature for 1 hour. Formaldehyde (37% aqueous solution, 0.32 mL, 3.7 mmol), acetic acid (0.21 mL, 3.7 mmol) and sodium acetate borohydride (0.78 g, 3.7 mmol) were added in this order to the reaction mixture, and heated to reflux for one day. The temperature was reduced to room temperature, and 1N caustic soda solution (10 mL) was added thereto, followed by stirring for 30 minutes. The reaction mixture was extracted with methylene chloride, and the organic layer was washed with distilled water once, and then dried over anhydrous magnesium sulfate. The solvent was removed by reduced pressure evaporation to obtain a light yellow oily liquid, which was purified by flash chromatography (methylene chloride:methanol=9:1) to obtain a light yellow oily liquid (0.17 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for one day
  3. customwas reduced to room temperature
  4. stirringby stirring for 30 minutes
  5. extractionThe reaction mixture was extracted with methylene chloride
  6. washthe organic layer was washed with distilled water once
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed by reduced pressure evaporation
  9. customto obtain a light yellow oily liquid, which
  10. customwas purified by flash chromatography (methylene chloride:methanol=9:1)

Sources & evidence

ORD record
ord-289ec11016fa41268f728b5f48478230
Source dataset
uspto-grants-2015_09
Patent number
US09120771B2

Reaction notes

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