Sodium Hydroxide → 1-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-amine

HRID 451461Notes

Reaction equation

HRID 451461 reaction equation
Cl.Cl.[CH3:3][C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11][CH2:10]2)[S:6][N:5]=1.[OH-].[Na+]>>[CH3:3][C:4]1[N:8]=[C:7]([N:9]2[CH2:10][CH2:11][CH:12]([NH2:15])[CH2:13][CH2:14]2)[S:6][N:5]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 673442811-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-amine dihydrochloride

Product 1

HCID 583978761-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-amine

Procedure

1-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-amine dihydrochloride (see example 36b, 2.3 g, 8.48 mmol) was neutralized with 2 N NaOH solution, The water layer was extracted three times with CH2Cl2 and three times with ethyl acetate, the combined organic phases were dried over Na2SO4, filtered and the solvents were evaporated. The crude product was purified by flash chromatography with CH2Cl2 and MeOH over a 50 g Si—NH2 column. The title compound was isolated as a light yellow oil (1.2 g, 71%).

Workup

  1. extractionThe water layer was extracted three times with CH2Cl2 and three times with ethyl acetate
  2. dry with materialthe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvents were evaporated
  5. customThe crude product was purified by flash chromatography with CH2Cl2 and MeOH over a 50 g Si—NH2 column

Sources & evidence

ORD record
ord-9734e21d11de4deeb00f28af8d2fbf88
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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