1,5-Diphenylpentan-3-one → 1-Amino-3-[1,5-di-(phenyl)-3-pentylamino]-2-propanol

HRID 443528

Reaction equation

HRID 443528 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](=O)[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][CH2:20][CH:21]([OH:24])[CH2:22][NH2:23].[H][H]>[Pt]=O.C(O)C>[NH2:19][CH2:20][CH:21]([OH:24])[CH2:22][NH:23][CH:9]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 214961,5-Diphenylpentan-3-oneHCID 611571,3-Diamino-2-propanolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 234678011-Amino-3-[1,5-di-(phenyl)-3-pentylamino]-2-propanol

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent2×

Procedure

A solution of 1,5-di-(phenyl)-3-pentanone (9.5 g., 0.04 mole) in 50 cc. of anhydrous ethanol is added dropwise over about 20 minutes to a stirred solution of 1,3-diamino-2-hydroxypropane (25 g., 0.27 mole) in 200 cc. of ethanol. The resulting mixture is then heated at reflux for about two hours, allowed to cool, 1.0 g. platinum oxide added, and the mixture reduced under a 40 psi hydrogen atmosphere until hydrogen uptake ceases. The mixture is then filtered from the catalyst, concentrated in vacuo to remove the ethanol, the residue taken up in ether (250 cc.), washed with water, dried over sodium sulfate, filtered and concentrated in vacuo to yield the product 1-amino-3-[1,5-di-(phenyl)-3-pentylamino]-2-propanol.

Workup

  1. temperatureThe resulting mixture is then heated
  2. temperatureat reflux for about two hours
  3. temperatureto cool
  4. filtrationThe mixture is then filtered from the catalyst
  5. concentrationconcentrated in vacuo
  6. customto remove the ethanol
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c1bba6f9a0740a2934ade15aec69a43
Source dataset
uspto-grants-1981_04
Patent number
US04260760

Linked notes

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