Sodium Bicarbonate → HCID 23366914, compound

HRID 1079406Notes

Reaction equation

HRID 1079406 reaction equation
Cl.[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:17]=[CH:16][C:15](N)=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)(=[O:4])[CH3:3].[C:19]([BH3-])#[N:20].[Na+].C(=O)(O)[O-].[Na+]>CO>[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:20][CH2:19][CH2:6][CH2:7][CH2:8][CH3:9])=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 23366893HCID 23366893, compound

Product 1

HCID 23366914HCID 23366914, compoundYield 149.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Acetyl-4-(4-aminophenyloxy)piperidine hydrochloride (2.5 g) obatined in Example 1, (2) was dissolved in methanol (20 ml) and to the solution were added sodium cyano borohydride (1.2 g) and pentylaldehyde (0.8 g) at room temperature. The mixture was stirred at room temperature for 1 hour. To the mixture was added aqueous saturated solution of sodium bicarbonate (50 ml) and the mixture was extracted with methylene chloride (50 ml×3). The combined extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (delveoping solvent: ethyl acetate/hexane=3/1 (v/v)) to obtain 1-acetyl-4-(4-pentylaminophenyloxy)piperidine (2.1 g) as white crystals, m.p. 69°-71° C.

Workup

  1. extractionthe mixture was extracted with methylene chloride (50 ml×3)
  2. extractionThe combined extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (delveoping solvent: ethyl acetate/hexane=3/1 (v/v))

Sources & evidence

ORD record
ord-62851ab7e9e743748bd206f4458e9aaf
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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