Triethylamine → HCID 57875896, compound

HRID 517823Notes

Reaction equation

HRID 517823 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.Br[CH2:12][C:13]#[N:14].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]([CH2:12][C:13]#[N:14])[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 8471TriethylamineHCID 11534BromoacetonitrileHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 122100571-Methylpiperidin-4-one hydrochloride

Product 1

HCID 57875896HCID 57875896, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation of the title compound was carried out according to General Method 8 by using p-tolylhydrazine hydrochloride (10 g, 63 mmol), bromo acetonitrile (7.56 ml, 63 mmol), triethylamine (19.1 g, 189 mmol) and N-methyl-4-piperidone hydrochloride (2.54 g, 17 mmol) in ethanol (30 ml) to obtain 1.8 g of 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetonitrile after purification on neutral alumina chromatography eluting with methanol-dichloromethane gradient. The TFA salt of this material was obtained by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 mL).

Sources & evidence

ORD record
ord-8215bd803c7b4f96b19715e77b996e72
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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