Triethylamine → HCID 57876039, compound

HRID 509690

Reaction equation

HRID 509690 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][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C.Cl.[CH3:28][N:29]1[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]1>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]2[N:9]([CH2:12][CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:32]3[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][C:31]=3[C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15440(2-Bromoethyl)cyclohexaneHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 122100571-Methylpiperidin-4-one hydrochloride

Product 1

HCID 57876039HCID 57876039, compoundYield 0.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation of the title compound was carried out according to General Method 8. 4-Chlorophenylhydrazine hydrochloride (1 g, 5.5 mmol), 1-bromo-2-cyclohexylethane (0.87 ml, 5.5 mmol), triethyl amine (2.31 ml, 16.6 mmol) and N-methyl-4-piperidone hydrochloride (810 mg, 5.5 mmol) were combined in ethanol (10 ml) to obtain 16 mg of 8-chloro-5-(2-cyclohexylethyl)-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole after purification on silica gel (230-400 mesh) chromatography eluting with acetone-hexane gradient. The free base was converted into its oxalate salt by treatment of oxalic acid (1 equiv.) in anhydrous THF.

Sources & evidence

ORD record
ord-f7391cc9c2684568ae66b70b164d434e
Source dataset
uspto-grants-2015_08
Patent number
US09096591B2

Linked notes

Loading…