Ammonia → N-[2-(4-(2-Hydroxyethoxy)-phenyl)-1-methylethyl]-2-(6-chloro-pyridin-2-yl)-morpholin-5-one

HRID 1494311Notes

Reaction equation

HRID 1494311 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([NH:14][CH2:15][CH:16]([OH:24])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[N:18]=2)[CH3:13])=[CH:7][CH:6]=1.C(N(CC)CC)C.Cl[CH2:33][C:34](Cl)=[O:35].[H-].[Na+].Cl.N>C(Cl)Cl.O>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([N:14]2[C:34](=[O:35])[CH2:33][O:24][CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[N:18]=3)[CH2:15]2)[CH3:13])=[CH:7][CH:6]=1

Participants

9

Reactant 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 24758Sodium hydrideHCID 14372898N-[2-(4-(2-Hydroxyethoxy)-phenyl)-1-methylethyl]-2-hydroxy-2-(6-chloro-pyridin-2-yl)-ethanamine

Product 1

HCID 14578858N-[2-(4-(2-Hydroxyethoxy)-phenyl)-1-methylethyl]-2-(6-chloro-pyridin-2-yl)-morpholin-5-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1 g (0.0285 mol) of N-[2-(4-(2-hydroxyethoxy)-phenyl)-1-methyl-ethyl]-2-hydroxy-2-(6-chloro-pyridin-2-yl)-ethanamine is dissolved in 40 ml of methylene chloride, 0.28 g (0.00285 mol) of triethylamine are added and then 0.322 g (0.00285 mol) of chloroacetyl chloride are added dropwise thereto with stirring in an ice bath. The reaction solution is stirred at ambient temperature for 40 minutes and evaporated down. The residue is dissolved in 10 ml of dimethylformamide, 110 mg (0.00234 mol) of 50-55% sodium hydride in oil are added and the resulting mixture is stirred for 30 minutes at ambient temperature. It is then carefully decomposed with 30 ml of water, acidified with 2N hydrochloric acid and then made alkaline with 2N ammonia. The product is extracted with methylene chloride, dried over sodium sulphate and concentrated by evaporation. The residue is purified over a silica gel column using ethyl acetate as eluant.

Workup

  1. stirringThe reaction solution is stirred at ambient temperature for 40 minutes
  2. customevaporated down
  3. dissolutionThe residue is dissolved in 10 ml of dimethylformamide
  4. stirringthe resulting mixture is stirred for 30 minutes at ambient temperature
  5. extractionThe product is extracted with methylene chloride
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation
  8. customThe residue is purified over a silica gel column

Sources & evidence

ORD record
ord-677f682001be43aaa0c8df927aff3f12
Source dataset
uspto-grants-1991_06
Patent number
US05026702

Reaction notes

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