1,3-Diamino-2-propanol → HCID 20319802, compound

HRID 866715Notes

Reaction equation

HRID 866715 reaction equation
[CH3:1][C:2]1([CH3:26])[CH:7]2[CH2:8][CH2:9][CH:4]([CH2:5][CH2:6]2)[CH:3]1[CH2:10][CH2:11][C:12](=O)[CH2:13][CH2:14][CH:15]1[C:20]([CH3:22])([CH3:21])[CH:19]2[CH2:23][CH2:24][CH:16]1[CH2:17][CH2:18]2.[NH2:27][CH2:28][CH:29]([OH:32])[CH2:30][NH2:31].[H][H]>C(O)C.[Pt]=O>[NH2:27][CH2:28][CH:29]([OH:32])[CH2:30][NH:31][CH:12]([CH2:13][CH2:14][CH:15]1[C:20]([CH3:22])([CH3:21])[CH:19]2[CH2:23][CH2:24][CH:16]1[CH2:17][CH2:18]2)[CH2:11][CH2:10][CH:3]1[C:2]([CH3:26])([CH3:1])[CH:7]2[CH2:8][CH2:9][CH:4]1[CH2:5][CH2:6]2

Participants

6

Reactant 3

HCID 611571,3-Diamino-2-propanolHCID 20319810HCID 20319810, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 20319802HCID 20319802, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent2×

Procedure

A solution of 1,5-di-(3,3-dimethylbicyclo[2.2.2]oct-2-yl)-3-pentanone (14.8 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 oily 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-(3,3-dimethylbicyclo[2.2.2]oct-2-yl)-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-fdc593ff2ecf46b8afc18f2fad20f0a9
Source dataset
uspto-grants-1978_07
Patent number
US04100193

Reaction notes

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