Methyl Isobutyl Ketone → HCID 86585567, compound

HRID 1634183Notes

Reaction equation

HRID 1634183 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][NH:13][CH2:14][C:5]=3[C:4]=2[CH:3]=1.C([CH:17]([CH2:21]Cl)[C:18]([NH2:20])=O)C.[C:23]([O-:26])([O-])=[O:24].[Na+].[Na+].[CH2:29](C(C)=O)[CH:30](C)C>[I-].[K+]>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH2:21][CH2:17][CH2:18][NH:20][C:23](=[O:24])[O:26][CH2:29][CH3:30])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 31574598-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleHCID 21802683HCID 21802683, compound

Product 1

HCID 86585567HCID 86585567, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 4875Potassium IodideCatalyst

Procedure

A mixture of 2,3,4,5-tetrahydro-8-methyl-1H-pyrido[4,3-b]indole, (0.079 mol), ethyl 3-chloropropanamide (0.097 mol), Na2CO3 (15 g) and potassium iodide (0.1 g) in methyl isobutyl ketone (350 ml) was stirred and refluxed overnight. The reaction mixture was filtered and the filtrate was evaporated, yielding 20 g (80%) of ethyl [3-(1,3,4,5-tetrahydro-8-methyl-2H-pyrido[4,3-b]indol-2-yl)propyl]carbamate (intermediate 10).

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-a17fe39a68a84fd9bf623dbf4b3b0b1a
Source dataset
uspto-grants-2003_01
Patent number
US06506768B2

Reaction notes

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