HCID 12875491, compound → 1-(Diphenylmethyl)-4-piperidinamine

HRID 2286683Notes

Reaction equation

HRID 2286683 reaction equation
[Br-].[NH2:2][C:3]1[CH:8]=[CH:7][N+:6]([CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[H][H]>[Pt](=O)=O.CO>[C:16]1([CH:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:6]2[CH2:7][CH2:8][CH:3]([NH2:2])[CH2:4][CH2:5]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 12875491HCID 12875491, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 128755351-(Diphenylmethyl)-4-piperidinamine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of 15.5 parts of 4-amino-1-(diphenylmethyl)-pyridinium bromide in 600 parts by volume of methanol is added 1.6 part of platinum dioxide catalyst and the resulting mixture is shaken with hydrogen at 60 psi pressure and room temperature for forty-two hours. The catalyst is then removed by filtration and the filtrate evaporated to dryness in vacuo. The residue is suspended in 200 parts by volume of 10% sodium carbonate solution and extracted with three 200 parts by volume portions of methylene chloride. The methylene chloride extracts are combined, dried over anhydrous sodium sulfate and evaporated to dryness in vacuo. The solid residue obtained is triturated with 250 parts by volume of anhydrous ethyl ether, filtered and the filtrate evaporated to yield 1-(diphenylmethyl)-4-piperidinamine, as a colorless solid melting at about 84°-95° C. This compound is represented by the following structural formula. ##STR20##

Workup

  1. customThe catalyst is then removed by filtration
  2. customthe filtrate evaporated to dryness in vacuo
  3. extractionextracted with three 200 parts by volume portions of methylene chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness in vacuo
  6. customThe solid residue obtained
  7. customis triturated with 250 parts by volume of anhydrous ethyl ether
  8. filtrationfiltered
  9. customthe filtrate evaporated

Sources & evidence

ORD record
ord-efa1a145edcc48e5b0bd333496ea59be
Source dataset
uspto-grants-1981_05
Patent number
US04267318

Reaction notes

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