2-Chloro-1-piperidine-1-yl-ethanone → 2-(1,2,3,4-Tetrahydro-8-iodo-2-methylpyrido[4,3-b]indol-5-yl)-1-(piperidin-1-yl)ethanone

HRID 574590

Reaction equation

HRID 574590 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.Cl[CH2:17][C:18]([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:19]>C1COCC1>[I:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:17][C:18]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])[C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 2223122-Chloro-1-piperidine-1-yl-ethanoneHCID 594549742,3,4,5-Tetrahydro-8-iodo-2-methyl-1h-pyrido[4,3-b]indole

Product 1

HCID 578763662-(1,2,3,4-Tetrahydro-8-iodo-2-methylpyrido[4,3-b]indol-5-yl)-1-(piperidin-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride was washed with hexane for removal of oil and dried under vacuum. Then sodium hydride was taken in THF. To this solution 8-iodo-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (100 mg, 0.32 mmol) in THF was added drop wise at 0° C. Then reaction mixture stirred for 0.5 h. The solution of 2-chloro-1-(piperidin-1-yl)ethanone in THF was added drop wise in reaction mixture. Then reaction mixture stirred at rt for 2 h. Reaction monitored by TLC, after completion of reaction, reaction mixture quench with ice-water. THF was evaporated and aqueous layer was extracted with ethyl acetate. Organic layer was dried over anhydrous sodium sulphate. The crude compound was purified by column chromatography to gives 25 mg of desired compound. Out of that 5 mg was stirred with ethanolic HCl to give HCl salt of 2-(8-iodo-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(piperidin-1-yl)ethanone.

Workup

  1. washSodium hydride was washed with hexane for removal of oil
  2. customdried under vacuum
  3. customThen reaction mixture
  4. customwise in reaction mixture
  5. customThen reaction mixture
  6. stirringstirred at rt for 2 h
  7. customReaction
  8. customafter completion of reaction, reaction mixture
  9. customquench with ice-water
  10. customTHF was evaporated
  11. extractionaqueous layer was extracted with ethyl acetate
  12. dry with materialOrganic layer was dried over anhydrous sodium sulphate
  13. customThe crude compound was purified by column chromatography

Sources & evidence

ORD record
ord-cadcb4a181ee4d57a784f2156db5917d
Source dataset
uspto-grants-2015_05
Patent number
US09034880B2

Linked notes

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