1'-Benzylspiro[indoline-3,4'-piperidine] → 4-(1'-Benzylspiro[indoline-3,4'-piperidin]-1-yl)-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinoline

HRID 585367Notes

Reaction equation

HRID 585367 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@H:11](O)[CH2:10][C@@H:9]1[CH3:19])=[O:7].[CH2:25]([N:32]1[CH2:37][CH2:36][C:35]2([C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[NH:39][CH2:38]2)[CH2:34][CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:25]([N:32]1[CH2:37][CH2:36][C:35]2([C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[N:39]([CH:11]3[C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[N:8]([C:6](=[O:7])[C:5]4[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:9]([CH3:19])[CH2:10]3)[CH2:38]2)[CH2:34][CH2:33]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 166410281'-Benzylspiro[indoline-3,4'-piperidine]HCID 69774154cis-1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol

Product 1

HCID 223392354-(1'-Benzylspiro[indoline-3,4'-piperidin]-1-yl)-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolineYield 52.4%

Procedure

Starting with cis-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol (400 mg, 1.22 mmol) prepared in Reference Example 1 and 1′-benzylspiro[indoline-3,4′-piperidine] (849 mg, 3.05 mmol), the same procedure as shown in Example 1 was repeated to give the titled compound (376 mg, yield: 44%) as a colorless oil. (cis:trans=1:1.5)

Sources & evidence

ORD record
ord-41b24b28573b4c52889c841e1d77e01b
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Reaction notes

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