Triethylamine → 5-(4-fluorophenethyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 509686

Reaction equation

HRID 509686 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19]Br)=[CH:14][CH:13]=1.C(N(CC)CC)C.Cl.[CH3:29][N:30]1[CH2:35][CH2:34][C:33](=O)[CH2:32][CH2:31]1>C(O)C>[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][N:8]2[C:5]3[CH:6]=[CH:7][C:2]([CH3:10])=[CH:3][C:4]=3[C:32]3[CH2:31][N:30]([CH3:29])[CH2:35][CH2:34][C:33]2=3)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 5731534-Fluorophenethyl bromideHCID 122100571-Methylpiperidin-4-one hydrochloride

Product 1

HCID 441263265-(4-fluorophenethyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleYield 1.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation of the title compound was carried out according to General Method 8. p-Tolylhydrazine hydrochloride (312 mg, 1.9 mmol), 4-fluorophenyl ethyl bromide (400 mg, 1.9 mmol), triethyl amine (0.264 ml, 1.9 mmol) and N-methyl-4-piperidone hydrochloride (424 mg, 2.8 mmol) were combined in ethanol (3 ml) to obtain 10 mg of 5-(4-fluorophenethyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole after purification by silica gel chromatography (100-200 mesh or 230-400 mesh) using ethyl acetate-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-016f197500504945b69cd2ab38933a83
Source dataset
uspto-grants-2015_08
Patent number
US09096591B2

Linked notes

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