Phenethyl bromide → 2,2,2-trichloroethyl 3,4-dihydro-8-methyl-5-phenethyl-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 574402Notes

Reaction equation

HRID 574402 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.[C:11]1([CH2:17][CH2:18]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.O=[C:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][C:38]([Cl:41])([Cl:40])[Cl:39])=[O:35])[CH2:30][CH2:29]1>C(O)C>[CH3:10][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([CH2:18][CH2:17][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][C:38]([Cl:41])([Cl:39])[Cl:40])=[O:35])[CH2:30][C:29]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 7666Phenethyl bromideHCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 152523022,2,2-Trichloroethyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 578759012,2,2-trichloroethyl 3,4-dihydro-8-methyl-5-phenethyl-1H-pyrido[4,3-b]indole-2(5H)-carboxylateYield 21.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation of the title compound was carried out according to General Method 8. p-Tolylhydrazine hydrochloride (10 g, 63 mmol), 2-phenyl ethyl bromide (11.6 g, 63 mmol), triethyl amine (19.4 g, 189 mmol) and 2,2,2-trichloroethyl 4-oxopiperidine-1-carboxylate (452 mg, 2 mmol) were taken in ethanol (10 ml) at 90° C. for 3 h to obtain 200 mg of 2,2,2-trichloroethyl 3,4-dihydro-8-methyl-5-phenethyl-1H-pyrido[4,3-b]indole-2(5H)-carboxylate after purification on silica gel (230-400 mesh) chromatography eluting with methanol-dichloromethane gradient.

Sources & evidence

ORD record
ord-a73acc6aa0f340a8876167edaf309535
Source dataset
uspto-grants-2015_05
Patent number
US09034880B2

Reaction notes

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