Ammonium formate → (S)-4-[2-Hydroxy-3-(N,N-dibenzylamino)propoxy]-1,3-dihydro-2H-benzimidazol-2-one

HRID 1386900Notes

Reaction equation

HRID 1386900 reaction equation
[OH:1][CH:2]([CH2:15][N:16]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:3][O:4][C:5]1[C:13]2[NH:12][C:11](=[O:14])[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.C([O-])=O.[NH4+]>CO.[Pd]>[OH:1][C@@H:2]([CH2:15][N:16]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:3][O:4][C:5]1[C:13]2[NH:12][C:11](=[O:14])[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 211830614-[2-Hydroxy-3-(N,N dibenzylamino)propoxy]-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 54425116(S)-4-[2-Hydroxy-3-(N,N-dibenzylamino)propoxy]-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-[2-Hydroxy-3-(N,N dibenzylamino)propoxy]-1,3-dihydro-2H-benzimidazol-2-one (4.35 g, 10.8 mmol) was dissolved in methanol (200 mL) and treated with a vast excess of ammonium formate (13.0 g, 0.21 mol), followed by 10% palladium on carbon (1.5 g). The suspension was stirred at reflux for 3 hours. After cooling the suspension, the reaction mixture was filtered through Celite. The filtrate concentrated in vacuo to a pale brown oil which slowly crystallized upon standing. The resulting solid was triturated using chloroform containing methanol and filtered to give 1.56 g (65%) as the desired product of a pale grey solid. NMR. MS.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureAfter cooling the suspension
  3. filtrationthe reaction mixture was filtered through Celite
  4. concentrationThe filtrate concentrated in vacuo to a pale brown oil which
  5. customslowly crystallized
  6. customThe resulting solid was triturated
  7. additioncontaining methanol
  8. filtrationfiltered

Sources & evidence

ORD record
ord-d6e1c6cc2fb042c0a26a721975591b13
Source dataset
uspto-grants-2001_07
Patent number
US06265581B1

Reaction notes

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