Acetic Acid → N-[2-(4-(2-Hydroxyethoxy)-phenyl)-1-methylethyl]-2-hydroxy-2-(6-chloro-pyridin-2-yl)-ethanamine

HRID 1494310노트

반응식

HRID 1494310 반응식
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[N:6]=1)[CH2:3][NH2:4].[OH:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](=O)[CH3:24])=[CH:18][CH:17]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[OH:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[N:6]=2)[CH3:24])=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 145788522-Amino-1-(6-chloropyridin-2-yl)ethan-1-olHCID 145788571-(4-(2-Hydroxyethoxy)phenyl)propan-2-one

생성물 1

HCID 14372898N-[2-(4-(2-Hydroxyethoxy)-phenyl)-1-methylethyl]-2-hydroxy-2-(6-chloro-pyridin-2-yl)-ethanamine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

21.2 g (0.122 mol) of 2-hydroxy-2-(6-chloro-pyridin-2-yl)-ethanamine and 21 g (0.108 mol) of 1-(4-(2-hydroxyethoxy)-phenyl)-propan-2-one are dissolved in 500 ml of absolute methanol, mixed with 7.3 g (0.122 mol) of acetic acid and 7.2 g (0.114 mol) of sodium cyanoborohydride and stirred overnight at ambient temperature. Then 300 ml of methanol are distilled off in vacuo, diluted with 400 ml of water, acidified with hydrochloric acid and then extracted three times with 250 ml of methylene chloride. The aqueous phase is then made alkaline with ammonia and extracted with methylene chloride. The organic phase obtained is dried over sodium sulphate and concentrated by evaporation, and the oil obtained initially crystallises out after a short time.

후처리

  1. distillationThen 300 ml of methanol are distilled off in vacuo
  2. additiondiluted with 400 ml of water
  3. extractionextracted three times with 250 ml of methylene chloride
  4. extractionextracted with methylene chloride
  5. customThe organic phase obtained
  6. dry with materialis dried over sodium sulphate
  7. concentrationconcentrated by evaporation
  8. customthe oil obtained initially
  9. customcrystallises out after a short time

출처 및 근거

ORD 기록
ord-eb00a913543c42b3bc1fe5b3185ac521
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05026702

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