1-(2-Hydroxyethyl)piperazine → HCID 19814273, compound

HRID 466610Notes

Reaction equation

HRID 466610 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[CH2:13])[C:11]3([CH2:18][CH2:17][N:16]([C:19](OC4C=CC=CC=4)=[O:20])[CH2:15][CH2:14]3)[O:10][C:9]2=[O:28])=[CH:4][CH:3]=1.[OH:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12](=[CH2:13])[C:11]3([CH2:14][CH2:15][N:16]([C:19]([N:35]4[CH2:36][CH2:37][N:32]([CH2:31][CH2:30][OH:29])[CH2:33][CH2:34]4)=[O:20])[CH2:17][CH2:18]3)[O:10][C:9]2=[O:28])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 19814389HCID 19814389, compound

Product 1

HCID 19814273HCID 19814273, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A mixture containing 4.0 g of 3-(4-chlorophenyl)-4-methylene-2-oxo-8-phenoxycarbonyl-1-oxa-3,8-diazaspiro[4,5]decane and 6.13 ml of N-(2-hydroxyethyl)piperazine in 20 ml of ortho-xylene is refluxed under nitrogen for 60 hours. After cooling down, the reaction mixture is diluted with 20 ml of xylene and the organic solution is washed first with an aqueous saturated sodium chloride solution containing 5% by weight of sodium hydroxide and then with aqueous saturated sodium chloride solution. After drying over anhydrous magnesium sulfate and then evaporating the solvent under reduced pressure the crude product obtained is recrystallized from a mixture of benzene and hexane under clarifying by activated carbon to give the title compound in 67% yield, m.p.: 185°-186° C.

Workup

  1. temperatureis refluxed under nitrogen for 60 hours
  2. temperatureAfter cooling down
  3. washthe organic solution is washed first with an aqueous saturated sodium chloride solution
  4. additioncontaining 5% by weight of sodium hydroxide
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customevaporating the solvent under reduced pressure the crude product
  7. customobtained
  8. customis recrystallized from a mixture of benzene and hexane under clarifying by activated carbon

Sources & evidence

ORD record
ord-d252204c1c1e45a58c4271b354de08da
Source dataset
uspto-grants-1992_10
Patent number
US05157038

Reaction notes

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