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

HRID 1388915
ノート
印刷プレビュー

反応式

HRID 1388915 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic Acid2 回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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0239fe97f5d549518ea66ba80c9255f7
出典データセット
uspto-grants-1984_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04434174

反応ノート

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