Acetic Acid → HCID 19029014, compound

HRID 975123Notes

Reaction equation

HRID 975123 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][N:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:23][CH2:22]3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][NH:10][CH2:9]2)=[CH:4][CH:3]=1.C=O.[C:35]([BH3-])#N.[Na+].C(O)(=O)C>C(#N)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:18][CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][N:24]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:25][CH2:26]3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][N:10]([CH3:35])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 19028848HCID 19028848, compound

Product 1

HCID 19029014HCID 19029014, compoundYield 154%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(p-chlorophenyl)-4-[3-(4-phenylpiperazin-1-yl)propyl]-1,2,3,4-tetrahydroisoquinoline (0.7 g) in acetonitrile (15 ml) was added formalin (0.64 ml). Then, sodium cyanoborohydride (0.16 g) was added portionwise with stirring. The mixture was stirred for 15 minutes, at the end of which time acetic acid was added dropwise until the solution became neutral. The mixture was further stirred for 2 hours and the reaction mixture was extracted with ethyl acetate-1N aqueous sodium hydroxide solution. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified by silica gel column chromatography and treated with hydrochloric acid to provide the title compound (0.6 g) as colorless powder.

Workup

  1. additionwas added dropwise until the solution
  2. stirringThe mixture was further stirred for 2 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate-1N aqueous sodium hydroxide solution
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by silica gel column chromatography
  8. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-97b7a2679dc14c59b163ccf3cd73a5f2
Source dataset
uspto-grants-1997_03
Patent number
US05607939

Reaction notes

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