Formic Acid → HCID 12527927, compound

HRID 1577005Notes

Reaction equation

HRID 1577005 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][CH:6]3[CH2:11][CH2:12][N:13]([CH2:15][CH2:16][CH2:17][C:18](=[O:26])[C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH2:14][CH:5]3[C:4]=2[CH:3]=1.[CH:27](O)=O.C=O.[OH-].[Na+]>O>[CH3:27][N:7]1[C:8]2[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=2[CH:5]2[CH2:14][N:13]([CH2:15][CH2:16][CH2:17][C:18](=[O:26])[C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[CH2:12][CH2:11][CH:6]12

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 3044949HCID 3044949, compound

Product 1

HCID 12527927HCID 12527927, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8-methyl-2-[γ-(p-fluorobenzoyl)propyl]-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (7.5 g), formic acid (2.7 g) and formalin (2.2 g) is refluxed for 3 hours. After cooling, to the reaction mixture is added water, and the mixture is made alkaline with aqueous sodium hydroxide and extracted with benzene. The benzene layer is dried over anhydrous sodium sulfate and concentrated. The resulting residue is treated with ethanolic hydrogen chloride in the same manner as described in Example 1 (1) to give the dihydrochloride of the titled compound (4.1 g), m.p. 140° - 145°C (recrystallized from aqueous ethanol).

Workup

  1. temperatureis refluxed for 3 hours
  2. temperatureAfter cooling, to the reaction mixture
  3. extractionextracted with benzene
  4. dry with materialThe benzene layer is dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionThe resulting residue is treated with ethanolic hydrogen chloride in the same manner
  7. customto give
  8. customthe dihydrochloride of the titled compound (4.1 g), m.p. 140° - 145°C (recrystallized from aqueous ethanol)

Sources & evidence

ORD record
ord-ada0d4be43aa4a14a4db12af7cede76e
Source dataset
uspto-grants-1976_09
Patent number
US03983239

Reaction notes

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