Triethylamine → HCID 23932524, compound

HRID 517819Notes

Reaction equation

HRID 517819 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(N(CC)CC)C.Cl.[CH3:27][N:28]1[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1>C(O)C>[CH3:27][N:28]1[CH2:33][CH2:32][C:31]2[N:8]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]3[CH:4]=[CH:3][C:2]([CH3:10])=[CH:7][C:6]=3[C:30]=2[CH2:29]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 68320Ethyl 3-bromopropionateHCID 122100571-Methylpiperidin-4-one hydrochloride

Product 1

HCID 23932524HCID 23932524, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Preparation of the title compound was carried out according to General Method 1. p-Tolylhydrazine hydrochloride (20 g, 126 mmol), ethyl 3-bromopropionate (22.8 g, 126 mmol) and triethylamine (38.1 g, 378 mmol) in ethanol (200 ml) were stirred at 25° C. for 1 h after which the contents were heated at 90° C. for 3 h. The contents were cooled to 25° C. and evaporated to dryness. The residue was acidified with ethanolic HCl and the volatiles were removed under reduced pressure. Ethanol (200 mL) was added followed by N-methyl-4-piperidone hydrochloride (2.87 g, 18.9 mmol). Heating was continued at 90° C. for 16 h. The contents were concentrated in vacuo, basified by adding saturated aqueous NaHCO3, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by chromatography on neutral alumina using methanol-dichloromethane gradient to obtain 1.5 g of ethyl 3-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)propanoate.

Workup

  1. temperatureThe contents were cooled to 25° C.
  2. customevaporated to dryness
  3. customthe volatiles were removed under reduced pressure
  4. additionEthanol (200 mL) was added
  5. temperatureHeating
  6. concentrationThe contents were concentrated in vacuo
  7. additionby adding saturated aqueous NaHCO3
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customThe crude product was purified by chromatography on neutral alumina

Sources & evidence

ORD record
ord-5dc6519323e6419eba0b038eb81997ed
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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