Ethanolamine → N-(2-hydroxyethyl)nicotinamide

HRID 34900

반응식

HRID 34900 반응식
C1(=O)N([N:6]2[CH:14]=[CH:13][CH:12]=[C:8]([C:9]([O-:11])=O)[CH2:7]2)C(=O)CC1.[CH2:17]([CH2:19][NH2:20])[OH:18].C(N(C(C)C)CC)(C)C.C(N)C.CN(C=O)C.C([O-])(=O)C1C=CC=NC=1.ON1C(=O)CCC1=O>CN(C=O)C>[OH:18][CH2:17][CH2:19][NH:20][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[N:6][CH:7]=1

참가 물질

8

반응물 6

HCID 700Ethanolamine2회HCID 937NicotinateHCID 80170N-HydroxysuccinimideHCID 81531DiisopropylethylamineHCID 86742329N-succinimidyl-nicotinate2회HCID 86742330ethylamine DMF

생성물 1

HCID 72663N-(2-hydroxyethyl)nicotinamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The N-succinimidyl-nicotinate compound described in Example 1 was reacted with the hydrochloric salt of ethanolamine, available commercially in its radioactive form. The ethanolamine salt was dissolved in dried DMF and chilled in an ice bath. To the mixture was added an equimolar of diisopropylethylamine (DIEA) and stirred for 15 minutes. An equimolar solution of N-succinimidyl-nicotinate was added to the ethylamine-DMF mixture dropwise under a nitrogen atmosphere. As the nicotinate was added the mixture turned milky and was slurried for at least another half hour. The milky substance was the N-hydroxy-succinimide precipitating, which was filtered off. The DMF-mixture was washed with ether to remove any precipitant. The solvent mixture was removed under high vaccum. The oily mixture was triturated with ether to yield a precipitant, N-(2-hydroxyethyl)nicotinamide. The radioactive compound was isolated and identified by its TLC.

후처리

  1. temperaturechilled in an ice bath
  2. customleast another half hour
  3. filtrationwas filtered off
  4. washThe DMF-mixture was washed with ether
  5. customto remove any precipitant
  6. customThe solvent mixture was removed under high vaccum
  7. customThe oily mixture was triturated with ether

출처 및 근거

ORD 기록
ord-b5b09e4205d74d908c6d4d8044e0f888
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04764462

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