1,2,3,6-Tetrahydro-4-phenylpyridine → HCID 21559968, compound

HRID 1578414Notes

Reaction equation

HRID 1578414 reaction equation
[C:1]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH3:17])=[CH:12][CH:13]=2)[CH:8]([CH2:18][CH2:19]Br)[CH:7]1[CH2:21][CH3:22])(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:23]1([C:29]2[CH2:30][CH2:31][NH:32][CH2:33][CH:34]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH2:43][CH2:44][NH:45][CH2:46][CH:47]=2)=[CH:38][CH:37]=1.[F:48][C:49]([F:63])([F:62])[C:50]1[CH:55]=[CH:54][C:53]([CH:56]2[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]2)=[CH:52][CH:51]=1>>[C:1]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH3:17])=[CH:12][CH:13]=2)[CH:8]([CH2:18][CH2:19][N:32]2[CH2:31][CH:30]=[C:29]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:34][CH2:33]2)[CH:7]1[CH2:21][CH3:22])(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:1]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH3:17])=[CH:12][CH:13]=2)[CH:8]([CH2:18][CH2:19][N:45]2[CH2:44][CH:43]=[C:42]([C:39]3[CH:40]=[CH:41][C:36]([Cl:35])=[CH:37][CH:38]=3)[CH2:47][CH2:46]2)[CH:7]1[CH2:21][CH3:22])(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:1]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH3:17])=[CH:12][CH:13]=2)[CH:8]([CH2:18][CH2:19][N:59]2[CH2:60][CH2:61][CH:56]([C:53]3[CH:54]=[CH:55][C:50]([C:49]([F:48])([F:62])[F:63])=[CH:51][CH:52]=3)[CH2:57][CH2:58]2)[CH:7]1[CH2:21][CH3:22])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 1857174-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridineHCID 124407024-(4-(Trifluoromethyl)phenyl)piperidineHCID 21559966HCID 21559966, compound

Product 3

HCID 21559968HCID 21559968, compoundHCID 54385492HCID 54385492, compoundHCID 54504784HCID 54504784, compound

Procedure

In the manner described in Example 5, reaction of 1-isobutyryl-2-ethyl-3-(2-bromoethyl)-5-ethoxyindoline with 4-phenyl-1,2,3,6-tetrahydropyridine, 4-(p-chlorophenyl)-1,2,3,6-tetrahydropyridine, or 4-(p-trifluoromethylphenyl)piperidine provides the corresponding 1-isobutyryl-2-ethyl-5-ethoxy-3-[2-(4-phenyl-3,6-dihydro-1(2H)-pyridyl)ethyl]indoline, 1-isobutyryl-2-ethyl-5-ethoxy-3-{2-[4-(p-chlorophenyl)-3,6-dihydro-1(2H)-pyridyl]ethyl} indoline, and 1-isobutyryl-2-ethyl-5-ethoxy-3-{2-[4-(p-trifluoromethylphenyl)piperidino]-ethyl} indoline.

Sources & evidence

ORD record
ord-411eb220951a4e509b51ad52de532eaa
Source dataset
uspto-grants-1976_02
Patent number
US03936464

Reaction notes

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