Sodium Hydroxide → 4-(Diphenylmethylene)piperidine

HRID 2250410Notes

Reaction equation

HRID 2250410 reaction equation
[OH-].[Na+].C(OC([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)C.C(=O)(O)N>O.C(O)C>[C:15]1([C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68905223HCID 68905223, compound

Product 1

HCID 27625334-(Diphenylmethylene)piperidineYield 75.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (15.85 g, 396 mmol) in water (30 mL) was added to the carbamate 1-ethoxycarbonyl 4-(diphenylmethylidene)piperidine 19 (11.47 g, 35.7 mmol) dissolved in ethanol (150 mL). The mixture was heated at reflux overnight. The reaction mixture was cooled to room temperature was then partitioned between water (100 mL) and ethyl acetate (150 mL). The mixture was stirred to dissolve the solid and the layers were separated. The organic layer was washed with brine (100 mL) and the separate aqueous layers were extracted with ethyl acetate (100 mL). The combined organic layers were dried with Na2SO4, filtered, and concentrated. The yellow oil was dried by high vacuum to give 6.7 g (75%) of 20 as a yellow-white waxy solid. 1H NMR was used to confirm the structure of the product. (Amine 22 was similarly prepared.)

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customwas then partitioned between water (100 mL) and ethyl acetate (150 mL)
  4. dissolutionto dissolve the solid
  5. customthe layers were separated
  6. washThe organic layer was washed with brine (100 mL)
  7. extractionthe separate aqueous layers were extracted with ethyl acetate (100 mL)
  8. dry with materialThe combined organic layers were dried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe yellow oil was dried by high vacuum

Sources & evidence

ORD record
ord-9b6ac1cb3c9448628f842aaa964f58f0
Source dataset
uspto-grants-2008_01
Patent number
US07317026B2

Reaction notes

Loading…