Water → HCID 178509146, compound

HRID 2095189Notes

Reaction equation

HRID 2095189 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11](=O)[C:12](=[N:15][NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]#[N:14])[CH2:6][CH2:5]O[CH2:3][CH2:2]1.[OH2:24].[NH2:25][NH2:26].O>CCOCC.C1COCC1>[N:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[C:12](=[N:15][NH:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:13]([NH2:14])=[N:25][N:26]=2)[CH2:6][CH2:5][O:24][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 86601978HCID 86601978, compound

Product 1

HCID 178509146HCID 178509146, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent

Procedure

The powder of 7-morpholin-4-yl-3-oxo-2-(phenylhydrazono)-heptanenitrile (510 mg, 1.6 mmole) and hydrazine hydrate (3.2 mmole) were suspended in 20 mL of ether:THF (1:1) and stirred at ambient temperature overnight. Water was added to the reaction and the mixture was extracted with ethyl acetate. The organic extracts were washed with saline. The volume of the organic solution was reduced which resulted in the precipitation of a yellow solid. The solution was filtered to yield 270 mg (51%) of the title compound as a yellow powder. MS (m/z, ES+): 329 (M+1, 100%); 1H NMR (ppm, 300 MHz, DMSO-d6) δ 11.58 (br s, 1H), 7.66 (m, 2H), 7.44 (m, 2H), 7.30 (m, 1H), 6.98 (br s, 2H), 3.51 (m, 4H), 2.79 (m, 2H), 2.20-2.33 (m, 5H), 1.72 (m, 2H), 1.47 (m, 2H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic extracts were washed with saline
  3. customresulted in the precipitation of a yellow solid
  4. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-ddc0b9cb867a4916b96f1543fab6b83a
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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