Triethylamine → HCID 57876091, compound

HRID 2195838Notes

Reaction equation

HRID 2195838 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.Br.Br[CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]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>[CH3:28][N:29]1[CH2:34][CH2:33][C:32]2[N:9]([CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:6]3[CH:5]=[CH:4][C:3]([CH3:2])=[CH:8][C:7]=3[C:31]=2[CH2:30]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 122100571-Methylpiperidin-4-one hydrochlorideHCID 201374851-(2-Bromoethyl)pyrrolidine--hydrogen bromide (1/1)

Product 1

HCID 57876091HCID 57876091, compoundYield 4.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation of the title compound was carried out according to General Method 8. 4-Methylphenylhydrazine hydrochloride (2 g, 12.6 mmol), 1-(2-bromoethyl)pyrrolidine hydrobromide (8.1 g, 31.5 mmol), triethyl amine (17.5 ml, 126 mmol) and N-methyl-4-piperidone hydrochloride (1.87 g, 12.6 mmol) were combined in ethanol (15 ml) to obtain 180 mg of 2,3,4,5-tetrahydro-2,8-dimethyl-5-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrido[4,3-b]indole after on purification on silica gel (230-400 mesh) chromatography eluting with acetone-hexane gradient. The free base was converted into its dioxalate salt by treatment of oxalic acid (2 equiv.) in anhydrous THF.

Sources & evidence

ORD record
ord-9a1d5ff3e86246ec823b46159a0b55f3
Source dataset
uspto-grants-2012_12
Patent number
US08338408B2

Reaction notes

Loading…