Acetic Acid → N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-1H-benzimidazole-1-propanamine oxalate

HRID 1388915Notes

Reaction equation

HRID 1388915 reaction equation
C([N:8]([CH2:21][CH:22]([OH:35])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([NH2:34])=[O:33])=[CH:27][CH:26]=1)[CH2:9][CH2:10][CH2:11][N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1)C1C=CC=CC=1.C(O)(=O)C.NC(=O)CC1C=CC(OCC(O)CNCCCN2C3C=CC=CC=3N=C2)=CC=1.[C:68]([OH:73])(=[O:72])[C:69]([OH:71])=[O:70]>[Pd].CO>[C:68]([OH:73])(=[O:72])[C:69]([OH:71])=[O:70].[NH2:34][C:32](=[O:33])[CH2:31][C:28]1[CH:29]=[CH:30][C:25]([O:24][CH2:23][CH:22]([OH:35])[CH2:21][NH:8][CH2:9][CH2:10][CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[CH:13]2)=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 971Oxalic AcidHCID 13066756N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-1H-benzimidazole-1-propanamineHCID 20469026N-benzyl-N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-1H-benzimidazole-1-propanamine

Product 1

HCID 20469042N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-1H-benzimidazole-1-propanamine oxalate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.5 gram of N-benzyl-N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-1H-benzimidazole-1-propanamine and 0.17 gram of 10% palladium on carbon in 30 ml. of glacial acetic acid was hydrogenated for 17 hours at room temperature and an initial pressure of 40 pounds per square inch. The reaction mixture was then filtered and the solvent was evaporated from the filtrate to leave a semi-solid which was N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-1H-benzimidazole-1-propanamine as a salt with acetic acid. This product was mixed with an equivalent of oxalic acid in methanol and the white solid obtained was recrystallized from methanol to give N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-1H-benzimidazole-1-propanamine oxalate melting at about 169°-174° C. This material was identical with the oxalic acid salt prepared from the product of Example 4.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customthe solvent was evaporated from the filtrate
  3. customto leave a semi-solid which
  4. customthe white solid obtained
  5. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-0239fe97f5d549518ea66ba80c9255f7
Source dataset
uspto-grants-1984_02
Patent number
US04434174

Reaction notes

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