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

HRID 2198331Notes

Reaction equation

HRID 2198331 reaction equation
Cl.ClC1C=CC(NN)=CC=1.BrCCC1CCC(C)(C)C1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]([CH2:30][CH2:31][CH:32]2[CH2:36][CH2:35][C:34]([CH3:38])([CH3:37])[CH2:33]2)N)=[CH:24][CH:23]=1.C(OC(OCC)CCCNC)C.ClC1C=C2[C:58](=CC=1)[N:57]([CH2:61][CH2:62][CH:63]1[CH2:67][CH2:66]C(C)(C)C1)C=C2CCNC.C=O.C(O)(C(F)(F)F)=O>C(#N)C.C(N(CC)CC)C>[Cl:21][C:22]1[CH:27]=[C:26]2[C:25](=[CH:24][CH:23]=1)[N:28]([CH2:30][CH2:31][CH:32]1[CH2:36][CH2:35][C:34]([CH3:38])([CH3:37])[CH2:33]1)[C:67]1[CH2:66][N:57]([CH3:58])[CH2:61][CH2:62][C:63]2=1

Participants

10

Reactant 7

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 139945474,4-Diethoxy-N-methylbutan-1-amineHCID 669116262-(5-chloro-1-(2-(3,3-dimethylcyclopentyl)ethyl)-1H-indol-3-yl)-N-methylethanamineHCID 669116941-(4-Chlorophenyl)-1-(2-(3,3-dimethylcyclopentyl)ethyl)hydrazineHCID 669117183-(2-Bromoethyl)-1,1-dimethylcyclopentane

Product 1

HCID 442424416-chloro-2,3,4,9-tetrahydro-2-methyl-9-(2-(3,3-dimethylcyclopentyl)ethyl)-1H-pyrido[3,4-b]indole

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

The title compound is prepared by following General Methods 1, 3 and 4 using 4-chlorophenylhydrazine hydrochloride, 3-(2-bromoethyl)-1,1-dimethylcyclopentane, and triethylamine (General Method 1), 1-(4-chlorophenyl)-1-(2-(3,3-dimethylcyclopentyl)ethyl)hydrazine and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3) and 2-(5-chloro-1-(2-(3,3-dimethylcyclopentyl)ethyl)-1H-indol-3-yl)-N-methylethanamine (Example 14), formaldehyde and TFA in acetonitrile (General Method 4).

Sources & evidence

ORD record
ord-775342ab5cb748408306a152d4ae5e94
Source dataset
uspto-grants-2012_12
Patent number
US08338447B2

Reaction notes

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