Ammonia → (+/-)-2-Amino-5-[3-[3-(piperidinomethyl)phenoxy]-2-methylpropylamino]-3,4-oxadiazole

HRID 4646Notes

Reaction equation

HRID 4646 reaction equation
[CH3:1][CH:2]([CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:15]=1)[CH2:3][NH:4][C:5]([NH:7][NH:8][C:9]([NH2:11])=[O:10])=O.N>P(Cl)(Cl)(Cl)=O>[CH3:1][CH:2]([CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:15]=1)[CH2:3][NH:4][C:5]1[O:10][C:9]([NH2:11])=[N:8][N:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 20151488N-[2-Methyl-3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1,2-hydrazine dicarboxamide

Product 1

HCID 558686(+/-)-2-Amino-5-[3-[3-(piperidinomethyl)phenoxy]-2-methylpropylamino]-3,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

7 mmol of N-[2-Methyl-3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1,2-hydrazine dicarboxamide in 30 ml of phosphorus oxychloride are stirred for 6 hours at 50°-60° C. When cooled, the reaction mixture is poured out on 300 ml of ice water and neutralized by the addition of concentrated ammonia solution with cooling. The product is extracted with ether and the combined ether extracts are washed, dehydrated and concentrated by evaporation. The solid residue is recrystallised from ether.

Workup

  1. temperatureWhen cooled
  2. temperaturewith cooling
  3. extractionThe product is extracted with ether
  4. washthe combined ether extracts are washed
  5. concentrationconcentrated by evaporation
  6. customThe solid residue is recrystallised from ether

Sources & evidence

ORD record
ord-19bba1e04b7a4a7cafd3ccb58c5285a5
Source dataset
uspto-grants-1988_02
Patent number
US04727081

Reaction notes

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