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Triethylamine → 4-Hydroxy-piperidine-1-carboxylic Acid 5-(4-chloro-benzoylamino)-pyridin-2-yl Ester

HRID 1179940
Notes
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Reaction equation

HRID 1179940 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1.C(NC1C=CC([O:33][C:34]([N:36]2[CH2:41][CH2:40][CH:39]([O:42][Si](C(C)(C)C)(C)C)[CH2:38][CH2:37]2)=O)=NC=1)(=O)C1C=CC=CC=1.C(N(CC)CC)C.CCCCCCC>CN(C)C=O>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:34]([N:36]3[CH2:41][CH2:40][CH:39]([OH:42])[CH2:38][CH2:37]3)=[O:33])=[N:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8900HeptaneHCID 695176994-(tert-Butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic Acid 5-benzoylamino-pyridin-2-yl EsterHCID 178522254HCID 178522254, compound

Product 1

HCID 695188084-Hydroxy-piperidine-1-carboxylic Acid 5-(4-chloro-benzoylamino)-pyridin-2-yl EsterYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-N-(6-hydroxy-pyridin-3-yl)-benzamide (0.50 g, 2.00 mmol), 4-(tert-butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic acid 5-benzoylamino-pyridin-2-yl ester (0.90 g, 2.00 mmol) and triethylamine (0.20 g, 2.00 mmol) in dimethylformamide (10 mL) was stirred overnight at room temperature. The solvent was evaporated in vacuo. The residue was dissolved in dichloromethane, filtered over a short pad of silicagel and washed with ethyl acetate:heptane 50:50. The solvent was evaporated in vacuo and the residue was redissolved in acetonitrile and hydrofluoric acid (min. 40% in water, 0.50 mL) was added. After stirring overnight at room temperature the solvent was evaporated in vacuo. Dichloromethane and triethylamine (1 mL) were added and the solution was extracted twice with water, dried over sodium sulphate, filtered and evaporated in vacuo. Crystallisation from ethyl acetate:heptane yielded the title compound (321 mg, 43% yield).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. filtrationfiltered over a short pad of silicagel
  4. washwashed with ethyl acetate:heptane 50:50
  5. customThe solvent was evaporated in vacuo
  6. dissolutionthe residue was redissolved in acetonitrile
  7. additionhydrofluoric acid (min. 40% in water, 0.50 mL) was added
  8. customwas evaporated in vacuo
  9. additionDichloromethane and triethylamine (1 mL) were added
  10. extractionthe solution was extracted twice with water
  11. dry with materialdried over sodium sulphate
  12. filtrationfiltered
  13. customevaporated in vacuo
  14. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-460f62993efe4dbb831209b7a98acc56
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07279470B2

Reaction notes

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