Formaldehyde → 2-(6-Chloro-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)-1-(4-methylpiperidin-1-yl)ethanone

HRID 2198333Notes

Reaction equation

HRID 2198333 reaction equation
Cl.ClC1C=CC(NN)=CC=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH2:20][C:21]([N:23]2[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]2)=[O:22])N)=[CH:14][CH:13]=1.C(OC(OCC)CCCNC)C.ClC1C=C2C(=CC=1)N(C[C:53]([N:55]1[CH2:60][CH2:59][CH:58](C)[CH2:57][CH2:56]1)=O)C=C2CCNC.C=O.C(O)(C(F)(F)F)=O>C(#N)C.C(N(CC)CC)C>[Cl:11][C:12]1[CH:17]=[C:16]2[C:15](=[CH:14][CH:13]=1)[N:18]([CH2:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]1)=[O:22])[C:57]1[CH2:56][N:55]([CH3:53])[CH2:60][CH2:59][C:58]2=1

Participants

9

Reactant 6

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 139945474,4-Diethoxy-N-methylbutan-1-amineHCID 669116502-(5-chloro-3-(2-(methylamino)ethyl)-1H-indol-1-yl)-1-(4-methylpiperidin-1-yl)ethanoneHCID 669116852-(1-(4-Chlorophenyl)hydrazinyl)-1-(4-methylpiperidin-1-yl)ethanone

Product 1

HCID 442425042-(6-Chloro-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)-1-(4-methylpiperidin-1-yl)ethanone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

The title compound is prepared by following General Methods 1, 3, and 4 by using 4-chlorophenylhydrazine hydrochloride, 1-(N-bromoacetyl)-4-methyl piperidine, and triethylamine (General Method 1), 2-(1-(4-chlorophenyl)hydrazinyl)-1-(4-methylpiperidin-1-yl)ethanone and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3), 2-(5-chloro-3-(2-(methylamino)ethyl)-1H-indol-1-yl)-1-(4-methylpiperidin-1-yl)ethanone, formaldehyde and TFA in acetonitrile (General Method 4).

Sources & evidence

ORD record
ord-e985ecad7f9a43819e5db87e1edd8e0a
Source dataset
uspto-grants-2012_12
Patent number
US08338447B2

Reaction notes

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