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

HRID 1902460
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HRID 1902460 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 176Acetic Acid2회HCID 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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aa3d28b7658c4f338df362e9161efc26
출처 데이터셋
uspto-grants-1982_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04363808

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