Dichloromethane → 1-{1-[2-Hydroxy-3-(2-nitro-3-pyridyloxy)-propyl]-4-piperidyl}-imidazolidin-2-one

HRID 444447Notes

Reaction equation

HRID 444447 reaction equation
[O:1]1[CH2:14][CH:2]1[CH2:3][O:4][C:5]1[C:6]([N+:11]([O-:13])=[O:12])=[N:7][CH:8]=[CH:9][CH:10]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([N:21]2[CH2:25][CH2:24][NH:23][C:22]2=[O:26])[CH2:17][CH2:16]1.C(Cl)Cl>C(O)(C)C>[OH:1][CH:2]([CH2:3][O:4][C:5]1[C:6]([N+:11]([O-:13])=[O:12])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([N:21]2[CH2:25][CH2:24][NH:23][C:22]2=[O:26])[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11183186Pyridine, 2-nitro-3-(oxiranylmethoxy)-(9CI)HCID 130317571-(Piperidin-4-yl)imidazolidin-2-one

Product 1

HCID 234637961-{1-[2-Hydroxy-3-(2-nitro-3-pyridyloxy)-propyl]-4-piperidyl}-imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 46.0 g of 3-(2,3-epoxy-propoxy)-2-nitropyridine and 35.0 g of 1-(4-piperidyl)-imidazolidin-2-one in 500 ml of isopropanol is refluxed for 2 hours. Working up analogously to Example 1 using methylene chloride as the extracting agent yields crude 1-{1-[2-hydroxy-3-(2-nitro-3-pyridyloxy)-propyl]-4-piperidyl}-imidazolidin-2-one, which after recrystallisation from isopropanol melts at 154°-158°.

Workup

  1. temperatureis refluxed for 2 hours

Sources & evidence

ORD record
ord-8c3f32fb951c4349a98e06e647d46c90
Source dataset
uspto-grants-1981_04
Patent number
US04264599

Reaction notes

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