Triethylamine → Ethyl 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanoate

HRID 517822Notes

Reaction equation

HRID 517822 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=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>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]2[N:9]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:31]3[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][C:30]=3[C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 68320Ethyl 3-bromopropionateHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 122100571-Methylpiperidin-4-one hydrochloride

Product 1

HCID 44159333Ethyl 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanoateYield 7.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation of the title compound was carried out according to General Method 1 by using 4-chlorophenylhydrazine hydrochloride (10 g, 55 mmol), ethyl 3-bromopropionate (7.2 mL, 55 mmol), triethylamine (23 mL, 165 mmol) and N-methyl-4-piperidone hydrochloride (8.3 g, 55 mmol) in ethanol (100 ml) to obtain 1.4 g of ethyl 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanoate after purification on neutral alumina chromatography eluting with dichloromethane-hexane gradient.

Sources & evidence

ORD record
ord-267fd06c0d5e4134bec629b4246adf7f
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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