Ammonium Hydroxide → 5-(6-Aminopyridin-3-yl)piperidin-2-one

HRID 595910Notes

Reaction equation

HRID 595910 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][N:10](COCC[Si](C)(C)C)[C:9]2=O)=[CH:4][CH:3]=1.[OH-:23].[NH4+:24]>CO.C1(C)C=CC=CC=1>[NH2:24][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:9][NH:10][C:11](=[O:23])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 131734604(6-Fluoropyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)piperidin-2-one

Product 1

HCID 1180454365-(6-Aminopyridin-3-yl)piperidin-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To -(6-fluoropyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)piperidin-2-one (290 mg, 0.894 mmol) in a steel bomb, ammonium hydroxide (34.8 μl, 0.894 mmol) solution was added (40% head volume remained). The steel bomb reactor was heated at 150° C. for 44 h (250 psi on pressure gauge). LCMS—0.23 min, MH+192.1 (without SEM); 0.66 min, MH+322.1 (with SEM). After diluted with MeOH and toluene, volatile materials were completely removed in vacuo. 5-(6-aminopyridin-3-yl)piperidin-2-one was used for the next step.

Workup

  1. customLCMS—0.23 min, MH
  2. custom0.66 min, MH
  3. customwere completely removed in vacuo

Sources & evidence

ORD record
ord-ab11cc6df8af47e69d2cc0cfc725a106
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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