Acetic Acid → HCID 1378330, compound

HRID 2301143Notes

Reaction equation

HRID 2301143 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:29]([N:36]1[CH2:41][CH2:40][CH2:39][CH2:38][C:37]1=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[OH-].[Na+]>ClC(Cl)C>[CH2:29]([N:36]1[CH2:41][CH2:40][CH:39]([N:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)[CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 70461,2,3,4-TetrahydroisoquinolineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 51700761-Benzyl-2-piperidone

Product 1

HCID 1378330HCID 1378330, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

1,2,3,4-Tetrahydroisoquinoline (700 mg, 5.3 mmol), acetic acid (3.2 g, 5.3 mmol), sodium triacetoxyborohydride (2.2 g, 11 mmol) and benzylpiperidone (1.0 g, 5.3 mmol) were stirred at room temperature for 3.5 hours in dichloroethane (7 ml). The reaction solution was alkalified by adding sodium hydroxide aqueous solution, the reaction product was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine and then dried with anhydrous sodium sulfate. The solvent was removed by evaporation from the organic layer under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 900 mg (3.0 mmol, 56% in yield) of the title compound.

Workup

  1. extractionthe reaction product was extracted with ethyl acetate
  2. washthe organic layer was washed with water and saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was removed by evaporation from the organic layer under a reduced pressure
  5. customthe thus obtained material was separated
  6. custompurified by a silica gel column chromatography
  7. customto obtain

Sources & evidence

ORD record
ord-5a2b5e4a98d84f66bf53de5d7dcea750
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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