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

HRID 585358Notes

Reaction equation

HRID 585358 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11](O)[CH2:10][CH2:9]1)=[O:7].[CH2:24]([N:31]1[CH2:36][CH2:35][C:34]2([C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[NH:38][CH2:37]2)[CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([N:31]1[CH2:36][CH2:35][C:34]2([C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]([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:19]=[CH:20][C:21]([O:22][CH3:23])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH2:9][CH2:10]3)[CH2:37]2)[CH2:33][CH2:32]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 166410281'-Benzylspiro[indoline-3,4'-piperidine]HCID 223392201-(3,4-Dimethoxybenzoyl)-1,2,3,4-tetrahydro-4-quinolinol

Product 1

HCID 223392184-(1'-Benzylspiro[indoline-3,4'-piperidin]-1-yl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydroquinolineYield 48.4%

Procedure

Starting with 1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-4-quinolinol (250 mg, 0.76 mmol) prepared in Reference Example 2 and 1′-benzylspiro[indoline-3,4′-piperidine] (532 mg, 1.91 mmol), the same procedure as shown in Example 1 was repeated to give the product of interest, i.e., 4-(1′-benzylspiro[indoline-3,4′-piperidin]-1-yl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydroquinoline (211 mg, yield: 48%) as a white crystal.

Sources & evidence

ORD record
ord-b50a2637bc7b43e48fd428d149209aa4
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Reaction notes

Loading…