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

HRID 1494310Notes

Reaction equation

HRID 1494310 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-eb00a913543c42b3bc1fe5b3185ac521
Source dataset
uspto-grants-1991_06
Patent number
US05026702

Reaction notes

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