4-Phenylpiperidine → HCID 21559958, compound

HRID 1578413Notes

Reaction equation

HRID 1578413 reaction equation
[C:1]([N:5]1[C:13]2[CH:12]=[C:11]3[O:14][CH2:15][O:16][C:10]3=[CH:9][C:8]=2[CH:7]([CH2:17][CH2:18]Br)[CH:6]1[CH3:20])(=[O:4])[CH2:2][CH3:3].[C:21]1([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([CH:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[CH:36][CH:35]=1.[F:46][C:47]([F:61])([F:60])[C:48]1[CH:53]=[CH:52][C:51]([C:54]2[CH2:55][CH2:56]NCC=2)=[CH:50][CH:49]=1>>[C:1]([N:5]1[C:13]2[CH:12]=[C:11]3[O:14][CH2:15][O:16][C:10]3=[CH:9][C:8]=2[CH:7]([CH2:17][CH2:18][N:30]2[CH2:31][CH2:32][CH:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:28][CH2:29]2)[CH:6]1[CH3:20])(=[O:4])[CH2:2][CH3:3].[C:1]([N:5]1[C:13]2[CH:12]=[C:11]3[O:14][CH2:15][O:16][C:10]3=[CH:9][C:8]=2[CH:7]([CH2:17][CH2:18][N:43]2[CH2:44][CH2:45][CH:40]([C:37]3[CH:36]=[CH:35][C:34]([Cl:33])=[CH:39][CH:38]=3)[CH2:41][CH2:42]2)[CH:6]1[CH3:20])(=[O:4])[CH2:2][CH3:3].[C:1]([N:5]1[C:13]2[CH:12]=[C:11]3[O:14][CH2:15][O:16][C:10]3=[CH:9][C:8]=2[CH:7]([CH2:17][CH2:18][N:30]2[CH2:29][CH:28]=[CH:56][CH2:55][CH:54]2[C:51]2[CH:50]=[CH:49][C:48]([C:47]([F:46])([F:60])[F:61])=[CH:53][CH:52]=2)[CH:6]1[CH3:20])(=[O:4])[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 698734-PhenylpiperidineHCID 12036134-(4-Chlorophenyl)piperidineHCID 12440708Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-HCID 21559977HCID 21559977, compound

Product 3

HCID 21559958HCID 21559958, compoundHCID 21559976HCID 21559976, compoundHCID 54020821HCID 54020821, compound

Procedure

In the manner described in Example 1, reaction of 5-propionyl-6-methyl-6,7-dihydro-7-(2-bromoethyl)-5H-1,3-dioxolo[4,5-f]indole with 4-phenylpiperidine, 4-(p-chlorophenyl)piperidine, or 1,2,3,6-tetrahydro-4-(α,α,α-trifluoro-p-tolyl)pyridine provides the corresponding 5-propionyl-6-methyl-6,7-dihydro-7-[2-(4-phenylpiperidino) ethyl]-5H-1,3-dioxolo[4,5-f]indole, 5-propionyl-6-methyl-6,7-dihydro-7-{2-[4(p-chlorophenyl)piperidino]ethyl}-5H-1,3-dioxolo-[4,5-f]-indole, and 5-propionyl-6-methyl-6,7-dihydro-7-{2-[3,6-dihydro-(α,α,α-trifluoro-p-tolyl)-1(2H)-pyridyl]ethyl}-5H-1,3-dioxolo[4,5-f]indole.

Sources & evidence

ORD record
ord-04261106b6794e838c10000248fcb3a0
Source dataset
uspto-grants-1976_02
Patent number
US03936464

Reaction notes

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