2-(2-Chlorophenoxymethyl)oxirane → 1-[2-(5-Carbamoyl-2-pyridyloxy)ethyl-amino]-3-(2-chloro-phenoxy)-2-propanol

HRID 2399154Notes

Reaction equation

HRID 2399154 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH:10]1[O:12][CH2:11]1.[NH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[CH:19][N:18]=1>C(O)(C)C>[C:21]([C:20]1[CH:24]=[CH:25][C:17]([O:16][CH2:15][CH2:14][NH:13][CH2:11][CH:10]([OH:12])[CH2:9][O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[N:18][CH:19]=1)(=[O:22])[NH2:23]

Participants

4

Reactant 2

HCID 1375002-(2-Chlorophenoxymethyl)oxiraneHCID 541029266-(2-Aminoethoxy)-nicotinic acid amide

Product 1

HCID 213331931-[2-(5-Carbamoyl-2-pyridyloxy)ethyl-amino]-3-(2-chloro-phenoxy)-2-propanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

9.2 g of 3-(2-chloro-phenyloxy)-1,2-epoxy-propane are added to a solution of 9.0 g of 6-(2-aminoethoxy)-nicotinic acid amide in 200 ml of isopropanol and the mixture is heated under reflux for 4 hours. After evaporating off the solvent under reduced pressure, 1-[2-(5-carbamoyl-2-pyridyloxy)ethyl-amino]-3-(2-chloro-phenoxy)-2-propanol is obtained; its hydrochloride melts at 202°-204° C. after recrystallisation from methanol.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 4 hours
  3. customAfter evaporating off the solvent under reduced pressure

Sources & evidence

ORD record
ord-3d0af546accb45b4a973389057a3737a
Source dataset
uspto-grants-1977_05
Patent number
US04027027

Reaction notes

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