Propargyl bromide → HCID 86634535, compound

HRID 517853Notes

Reaction equation

HRID 517853 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.[CH2:11](Br)[C:12]#[CH:13].C(N(CC)CC)C.Cl.[CH3:23][N:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1>C(O)C>[CH3:23][N:24]1[CH2:29][CH2:28][C:27]2[N:8]([CH2:13][C:12]#[CH:11])[C:5]3[CH:4]=[CH:3][C:2]([CH3:10])=[CH:7][C:6]=3[C:26]=2[CH2:25]1

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 122100571-Methylpiperidin-4-one hydrochloride

Product 1

HCID 86634535HCID 86634535, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-Tolylhydrazine hydrochloride (600 mg, 3.7 mmol), propargyl bromide (80 wt % solution in toluene, 0.34 ml, 3.7 mmol), triethylamine (1.5 ml, 11.3 mmol) and N-methyl-4-piperidone hydrochloride (316 mg, 2.1 mmol) were taken in ethanol (15 ml) to obtain 80 mg of 2, 3,4,5-tetrahydro-2,8-dimethyl-5-(prop-2-ynyl)-1H-pyrido[4,3-b]indole after purification on silica gel (230-400 mesh) chromatography, eluting with methanol-dichloromethane gradient. 1H NMR (CDCl3) 7.30-7.25 (d, 1H), 7.20 (s, 1H), 7.00-6.90 (d, 1H), 4.80 (s, 2H), 3.70 (s, 2H), 2.95 (m, 4H), 2.60 (s, 3H), 2.40 (s, 3H), 2.10-2.00 (t, 1H).

Sources & evidence

ORD record
ord-39ac2497599b4b288ff3131aee9669a1
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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