Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → chloro-2,3,4,5-tetrahydro-2-methyl-5-(2-morpholinoethyl)-1H-pyrido[4,3-b]indole

HRID 1465248Notes

Reaction equation

HRID 1465248 reaction equation
[ClH:1].Cl[C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.Br[CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(C1[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=1[N:24]([CH2:27]C)CC)C.Cl.CN1CCC(=O)CC1>C(O)C>[Cl:1][CH:23]1[C:29]2[C:7]3[CH:8]=[CH:3][CH:4]=[CH:5][C:6]=3[N:9]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:30]=2[CH2:31][CH2:32][N:24]1[CH3:27]

Participants

6

Reactant 4

HCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 15021014-(2-Bromoethyl)morpholineHCID 122100571-Methylpiperidin-4-one hydrochlorideHCID 18366426N,N,2-Triethylaniline

Product 1

HCID 86634532chloro-2,3,4,5-tetrahydro-2-methyl-5-(2-morpholinoethyl)-1H-pyrido[4,3-b]indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation of the title compound was carried out according to General Method 8. 4-Chlorophenylhydrazine hydrochloride (2 g, 11 mmol), 4-(2-bromoethyl)morpholine (2.1 g, 11 mmol), triethyl aniline (4.6 ml, 33 mmol) and N-methyl-4-piperidone hydrochloride (1.6 g, 11 mmol) were combined in ethanol (20 ml) to obtain 180 mg of -chloro-2,3,4,5-tetrahydro-2-methyl-5-(2-morpholinoethyl)-1H-pyrido[4,3-b]indole after purification on silica gel (230-400 mesh) chromatography eluting with acetone-hexane gradient. The free base was converted into its dioxalate salt by treatment of oxalic acid (2 equiv) in anhydrous THF.

Sources & evidence

ORD record
ord-4a4da1378e7f4aaba1f6232f828b4571
Source dataset
uspto-grants-2015_04
Patent number
US08999978B2

Reaction notes

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