Acetic Acid → HCID 20250792, compound

HRID 1284921Notes

Reaction equation

HRID 1284921 reaction equation
[CH3:1][N:2]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[C:5]2=[CH:6][CH:7]=[C:8]3[C:12]([NH:11][CH2:10][CH2:9]3)=[C:4]2[CH2:3]1.[C:22](O)(=O)C.C=O.C([BH3-])#N.[Na+]>CO>[CH3:22][N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]3[CH:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[F:21])[CH2:14][N:2]([CH3:1])[CH2:3][C:4]3=2)[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 20250789HCID 20250789, compound

Product 1

HCID 20250792HCID 20250792, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.3 g (0.00814 mol) of 8-methyl-6-(fluorophenyl)-2,3,6,7,8,9-hexahydro-1H-pyrido[4,3-g]indole are dissolved in 20 ml of MeOH, and 0.977 g (0.0163 mol) of acetic acid and 0.791 ml (0.00976 mol) of formalin are added at room temperature, with stirring. The reaction mixture is subsequently stirred for 1 hour and 1.53 g (0.0244 mol) of sodium cyanoborohydride are then added in several portions. In order to bring the reaction to completion, the mixture is subsequently stirred at room temperature for 1.5 hours. The solvent is then stripped off on a rotary evaporator, H2O is added to the residue and the mixture is rendered alkaline with 1N NaOH. The aqueous phase is extracted with CH2Cl2 and dried over NaSO4 and the solvent is evaporated off on a rotary evaporator. The oily residue is chromatographed on silica gel (silica gel 60 from E. Merck, Darmstadt) using an eluent mixture of: CH2Cl2 /MeOH (2.5:0.15). The product is dried in the absence of light in a desiccator over P2O5 at 10-2 bar.

Workup

  1. stirringThe reaction mixture is subsequently stirred for 1 hour
  2. customthe reaction to completion
  3. stirringthe mixture is subsequently stirred at room temperature for 1.5 hours
  4. customThe solvent is then stripped off on a rotary evaporator, H2O
  5. additionis added to the residue
  6. extractionThe aqueous phase is extracted with CH2Cl2
  7. dry with materialdried over NaSO4
  8. customthe solvent is evaporated off on a rotary evaporator
  9. customThe oily residue is chromatographed on silica gel (silica gel 60 from E. Merck, Darmstadt)
  10. additionan eluent mixture of: CH2Cl2 /MeOH (2.5:0.15)
  11. dry with materialThe product is dried in the absence of light in a desiccator over P2O5 at 10-2 bar

Sources & evidence

ORD record
ord-d1a9cfab9657484c8708c35cfe6c46e5
Source dataset
uspto-grants-1986_01
Patent number
US04564613

Reaction notes

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