2-Dibenzylamino-1,1-dimethylethylamine → 3-(2-Amino-1,1-dimethylethylamino)-1-(3-methylbenzimidazol-4-yloxy)-propan-2-ol

HRID 1607127Notes

Reaction equation

HRID 1607127 reaction equation
[O:1]1[CH2:15][CH:2]1[CH2:3][O:4][C:5]1[C:13]2[N:12]([CH3:14])[CH:11]=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.C([N:23](CC1C=CC=CC=1)[CH2:24][C:25]([NH2:28])([CH3:27])[CH3:26])C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[NH2:23][CH2:24][C:25]([NH:28][CH2:15][CH:2]([OH:1])[CH2:3][O:4][C:5]1[C:13]2[N:12]([CH3:14])[CH:11]=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 117778302-Dibenzylamino-1,1-dimethylethylamineHCID 198530372,3-Epoxy-1-(3-methylbenzimidazol-4-yloxy)-propaneHCID 178418361HCID 178418361, compound

Product 1

HCID 198529363-(2-Amino-1,1-dimethylethylamino)-1-(3-methylbenzimidazol-4-yloxy)-propan-2-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10.2 g. 2,3-Epoxy-1-(3-methylbenzimidazol-4-yloxy)-propane are added to 40.3 g. 2-dibenzylamino-1,1-dimethylethylamine (prepared analogously to H. G. Johnson, J.A.C.S., 68, 12/1946) in 300 ml. ethanol and the reaction mixture is stirred for 3 days at ambient temperature. The reaction mixture is now hydrogenated at 60° C. over 8 g. palladium-charcoal (10%) until the take up of hydrogen is finished. The catalyst is then filtered off with suction and the filtrate evaporated to dryness. The residue is chromatographed on silica gel with methanol/concentrated aqueous ammonia solution (95:5 v/v). The appropriate fractions are evaporated, the residue is taken up in methylene chloride and dried over anhydrous sodium sulphate and the solution is evaporated to dryness. There are obtained 8.7 g. (66% of theory) of the desired product as a pale yellow oil.

Workup

  1. customis now hydrogenated at 60° C. over 8 g
  2. filtrationThe catalyst is then filtered off with suction
  3. customthe filtrate evaporated to dryness
  4. customThe residue is chromatographed on silica gel with methanol/concentrated aqueous ammonia solution (95:5 v/v)
  5. customThe appropriate fractions are evaporated
  6. dry with materialdried over anhydrous sodium sulphate
  7. customthe solution is evaporated to dryness
  8. customThere are obtained 8.7 g

Sources & evidence

ORD record
ord-a57c0b9d57564d44bb79d1de126609cf
Source dataset
uspto-grants-1989_09
Patent number
US04863949

Reaction notes

Loading…