Tetrahydrofuran → 3-(Morpholin-4-ylmethyl)aniline

HRID 2095201Notes

Reaction equation

HRID 2095201 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([NH:14]N=[C:16]3[C:20]([C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=4)=N[N:18]=[C:17]3N)[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C1C[O:31]CC1.NN.[K]>CCO>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[O:31]=[C:20]([C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)[CH2:16][C:17]#[N:18]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 9321HydrazineHCID 5462222PotassiumHCID 178509140HCID 178509140, compound

Product 2

HCID 10964063-(Morpholin-4-ylmethyl)anilineHCID 157315353-Oxo-3-(pyridin-4-yl)propanenitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar manner, 4-[(3-morpholin-4-ylmethylphenyl)hydrazono]-5-pyridin-4-yl-4H-pyrazol-3-ylamine was prepared according the procedure described above in Paragraphs A and B with the following modifications: THF was used as the solvent to replace EtOH and the temperature was 55° C. for the hydrazine reaction. 3-Morpholin-4-ylmethylphenylamine (0.192 g, 1.0 mmol) and potassium salt of 3-oxo-3-pyridin-4-ylpropionitrile (0.276 g, 1.5 mmol) yielded 0.117 g of the product (32%). MS (m/z, ES+): 364.4 (M+1. 100%).

Sources & evidence

ORD record
ord-f2e9a98f704f4f3395fd3fbdc2c165dd
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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