Formaldehyde → 6-chloro-9-(2-cyclopentylethyl)-2,3, 4,9-tetrahydro-2-methyl-1H-pyrido[3,4-b]indole

HRID 1775945Notes

Reaction equation

HRID 1775945 reaction equation
Cl.ClC1C=CC(NN)=CC=1.BrCCC1CCCC1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]([CH2:28][CH2:29][CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)N)=[CH:22][CH:21]=1.C(OC(OCC)CCCNC)C.ClC1C=C2[C:54](=CC=1)[N:53]([CH2:57][CH2:58][CH:59]1[CH2:63][CH2:62]CC1)C=C2CCNC.C=O.C(O)(C(F)(F)F)=O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[Cl:19][C:20]1[CH:25]=[C:24]2[C:23](=[CH:22][CH:21]=1)[N:26]([CH2:28][CH2:29][CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)[C:63]1[CH2:62][N:53]([CH3:54])[CH2:57][CH2:58][C:59]2=1

Participants

10

Reactant 7

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 12711948(2-Bromoethyl)cyclopentaneHCID 139945474,4-Diethoxy-N-methylbutan-1-amineHCID 669116271-(4-Chlorophenyl)-1-(2-cyclopentylethyl)hydrazineHCID 669116392-(5-chloro-1-(2-cyclopentylethyl)-1H-indol-3-yl)-N-methylethanamine

Product 1

HCID 442424406-chloro-9-(2-cyclopentylethyl)-2,3, 4,9-tetrahydro-2-methyl-1H-pyrido[3,4-b]indole

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared by following General Methods 2, 3 and 4 using 4-chlorophenylhydrazine hydrochloride, (2-bromoethyl)cyclopentane, and tetra-n-butylammonium chloride (General Method 2), 1-(4-chlorophenyl)-1-(2-cyclopentylethyl)hydrazine (Example 4) and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3) and 2-(5-chloro-1-(2-cyclopentylethyl)-1H-indol-3-yl)-N-methylethanamine (Example 13), formaldehyde and TFA in acetonitrile (General Method 4).

Sources & evidence

ORD record
ord-9453cd90e89d49f1a234c0bf7f0d0b9e
Source dataset
uspto-grants-2016_02
Patent number
US09260429B2

Reaction notes

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