Ammonium Hydroxide → (+/-)-4-(6-Aminopyridin-3-yl)-1-methylpiperidin-2-one

HRID 595915Notes

Reaction equation

HRID 595915 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH3:14])[C:10](=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[OH-].[NH4+:17]>>[NH2:17][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH3:14])[C:10](=[O:15])[CH2:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 118054587(+/-)-4-(6-Fluoropyridin-3-yl)-1-methylpiperidin-2-one

Product 1

HCID 118054586(+/-)-4-(6-Aminopyridin-3-yl)-1-methylpiperidin-2-one

Conditions

Temperature
150 °C

Procedure

To a steel bomb, (+/−)-4-(6-fluoropyridin-3-yl)-1-methylpiperidin-2-one (341 mg, 1.638 mmol) was added followed by addition of ammonium hydroxide solution (0.00 mmol)—remaining 40% head space. The reactor was heat at 150° C. for 20 hr (internal pressure built up to 100 psi upon heating). After cooling down, the reaction was completed. The whole solvent (transferred to a flask) was removed in vacuo. Toluene was added and co-evaporated to remove water. The crude product, (+/−)-4-(6-aminopyridin-3-yl)-1-methylpiperidin-2-one, was used for the next step without further purification (87%). LCMS (m/z): 206.1 (MH+), 0.24 min.

Workup

  1. temperature(internal pressure built up to 100 psi upon heating)
  2. temperatureAfter cooling down
  3. customThe whole solvent (transferred to a flask) was removed in vacuo
  4. additionToluene was added
  5. customto remove water
  6. customThe crude product, (+/−)-4-(6-aminopyridin-3-yl)-1-methylpiperidin-2-one, was used for the next step without further purification (87%)
  7. custom206.1 (MH+), 0.24 min.

Sources & evidence

ORD record
ord-ee5ace42e62e4f73abb7710a3e252026
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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