HCID 13478150, compound → 4-(2-Methoxy-1,1-dimethylethyl)piperidine

HRID 2350915Notes

Reaction equation

HRID 2350915 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)([CH3:6])[CH2:3][O:4][CH3:5]>C(O)(=O)C.[Pt](=O)=O>[CH3:6][C:2]([CH:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1)([CH3:1])[CH2:3][O:4][CH3:5]

Participants

4

Reactant 1

HCID 13478150HCID 13478150, compound

Product 1

HCID 134781514-(2-Methoxy-1,1-dimethylethyl)piperidineYield 93.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 176Acetic AcidSolvent

Procedure

A solution of 4-(1,1-dimethyl-2-methoxyethyl)pyridine (10.0 g) in acetic acid (120 ml) was catalytically hydrogenated over platinum dioxide at 40 p.s.i. for 41 hours at from ambient temperature to 43° C. After 24 hours a further quantity of platinum dioxide was added, and a final addition was made after a further 8 hours. After a total of 41 hours the solution obtained after filtration of the catalyst was evaporated in vacuo and further evaporated after the addition of toluene to remove acetic acid. The resultant yellow oil was dissolved in dichloromethane and brought to pH12 with dilute aqueous sodium hydroxide solution. After saturation with sodium chloride, the organic phase was separated and the aqueous layer was re-extracted with five portions of dichloromethane. The combined organic solution was dried over anhydrous magnesium sulphate, and evaporated in vacuo to give 4-(1,1-dimethyl-2-methoxyethyl)piperidine (9.7 g) as a straw-coloured oil.

Workup

  1. additiona final addition
  2. waitwas made after a further 8 hours
  3. customAfter a total of 41 hours the solution obtained
  4. filtrationafter filtration of the catalyst
  5. customwas evaporated in vacuo
  6. customfurther evaporated
  7. additionafter the addition of toluene
  8. customto remove acetic acid
  9. dissolutionThe resultant yellow oil was dissolved in dichloromethane
  10. customAfter saturation with sodium chloride, the organic phase was separated
  11. extractionthe aqueous layer was re-extracted with five portions of dichloromethane
  12. dry with materialThe combined organic solution was dried over anhydrous magnesium sulphate
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-b20df5ff081a4b7090ad81edb445d31d
Source dataset
uspto-grants-1989_10
Patent number
US04871748

Reaction notes

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