Formaldehyde → Piperidine, 1-methyl-4-phenyl-

HRID 478651Notes

Reaction equation

HRID 478651 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]=O.[BH4-].[Na+]>COCCOC.C(O[Ti](OC(C)C)(OC(C)C)OC(C)C)(C)C>[C:1]1([CH:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 698734-PhenylpiperidineHCID 4311764Sodium borohydride

Product 1

HCID 202391Piperidine, 1-methyl-4-phenyl-

Reagents, catalysts & solvents 2

HCID 178460666HCID 178460666, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

4-Phenylpiperidine (12.4 mmol), paraformaldehyde (24.8 mmol) and tetraisopropoxy-titanium (12.4 mmol) are suspended in 1,2-dimethoxyethane (20 ml) and warmed to 60° C. for 30 minutes and stirred at rt for one additional hour. Sodium borohydride (12.4 mmol) is added in portions and the mixture is stirred at rt for 2 hours and at 60° C. for additional 3 hours. After cooling the solvent is evaporated and the residue is dissolved in a mixture of aqueous ammonia (60 ml) and ethyl acetate and filtered carefully. The mixture is extracted three times with ethyl acetate and the combined organic phases are dried over sodium sulfate and evaporated. A pale brown oil is obtained.

Workup

  1. stirringthe mixture is stirred at rt for 2 hours and at 60° C. for additional 3 hours
  2. temperatureAfter cooling the solvent
  3. customis evaporated
  4. dissolutionthe residue is dissolved in a mixture of aqueous ammonia (60 ml) and ethyl acetate
  5. filtrationfiltered carefully
  6. extractionThe mixture is extracted three times with ethyl acetate
  7. dry with materialthe combined organic phases are dried over sodium sulfate
  8. customevaporated
  9. customA pale brown oil is obtained

Sources & evidence

ORD record
ord-0a06a52daf6141dd9a21c8e6cde2d981
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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