Phenethyl bromide → HCID 57876160, compound

HRID 1465246Notes

Reaction equation

HRID 1465246 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.Cl.[CH:28]1([N:31]2[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]2)[CH2:30][CH2:29]1>C(O)C>[CH:28]1([N:31]2[CH2:36][CH2:35][C:34]3[N:8]([CH2:18][CH2:17][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:5]4[CH:4]=[CH:3][C:2]([CH3:10])=[CH:7][C:6]=4[C:33]=3[CH2:32]2)[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 7666Phenethyl bromideHCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 21535681HCID 21535681, compound

Product 1

HCID 57876160HCID 57876160, compoundYield 6.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation of the title compound was carried out according to General Method 8. p-Tolylhydrazine hydrochloride (500 mg, 3.1 mmol), 2-phenyl ethyl bromide (0.43 ml, 3.1 mmol), triethyl amine (0.43 ml, 3.1 mmol) and N-cyclopropyl-4-piperidone hydrochloride (650 mg, 4.72 mmol) were combined in ethanol (3 ml) to obtain 62 mg of 2-cyclopropyl-2,3,4,5-tetrahydro-8-methyl-5-phenethyl-1H-pyrido[4,3-b]indole after purification on neutral alumina 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-78efbaf6dbb64a33b10864e3bb2b6ec9
Source dataset
uspto-grants-2015_04
Patent number
US08999978B2

Reaction notes

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