Sodium Bicarbonate → N1-(3-Fluorobenzyl)-2-[1-[2-(2-methoxy-3-pyridyl)ethyl]-2-piperidyl]acetamide

HRID 1837753Notes

Reaction equation

HRID 1837753 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH:10]=O)=[CH:7][CH:6]=[CH:5][N:4]=1.[F:12][C:13]1[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=1)[CH2:16][NH:17][C:18](=[O:26])[CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][NH:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.C(O)(=O)C>[F:12][C:13]1[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=1)[CH2:16][NH:17][C:18](=[O:26])[CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][N:21]1[CH2:10][CH2:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22678592N1-(3-fluorobenzyl)-2-(2-piperidyl)acetamideHCID 226786312-(2-Methoxypyridin-3-yl)acetaldehyde

Product 1

HCID 22678505N1-(3-Fluorobenzyl)-2-[1-[2-(2-methoxy-3-pyridyl)ethyl]-2-piperidyl]acetamideYield 72.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

200 mg of 2-(2-methoxy-3-pyridyl)acetaldehyde, 400 mg of N1-(3-fluorobenzyl)-2-(2-piperidyl)acetamide, 440 mg of sodium triacetoxyborohydride and 0.12 ml of acetic acid were suspended in THF, followed by stirring at room temperature for 1 hour. An aqueous sodium bicarbonate was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate. After filtering off the drying agent, the solvent was evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=8:1, subsequently 4:1), to give 370 mg of a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over sodium sulfate
  3. filtrationAfter filtering off the drying agent
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-1f3e9f1675a04957b104b1127f707449
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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