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

HRID 1494310ノート

反応式

HRID 1494310 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eb00a913543c42b3bc1fe5b3185ac521
出典データセット
uspto-grants-1991_06
特許番号
US05026702

反応ノート

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