4-(2-Methoxyphenyl)piperidine → HCID 21839889, compound

HRID 725071Notes

Reaction equation

HRID 725071 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[N:14]2[CH3:23])[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C[O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[N:14]2[CH3:23])[CH2:10][CH2:11][N:35]2[CH2:36][CH2:37][CH:32]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[OH:25])[CH2:33][CH2:34]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 5447384-(2-Methoxyphenyl)piperidineHCID 218397793-(3,4-dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde

Product 1

HCID 21839889HCID 21839889, compoundYield 147%

Procedure

3-(3,4-Dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.368 g) was coupled to 4-(2-methoxyphenyl)piperidine (0.177 g) by a method similar to that described in Example 8. The reaction product was not purified by chromatography but converted to the corresponding hydrochloride salt as described in the Example 8 to afford the title compound (0.424 g); mp 150°-160° C.; MS: m/z=508(M+1); NMR(CD3SOCD3): 1.93-2.08 (m,4), 2.75 (m,1), 3.07 (s,3), 3.39 (m,5), 3.67-3.71 (m,32), 4.87 (d,1, J=3.7), 6.77-6.80 (m,3), 6.97-7.07 (m,3), 7.31 (m,1), 7.50 (m,2), 7.67 (m,1), 7.94 (d,1, J=7.7). Analysis for C29H29Cl2N2O2.1.5 HCl.0.5 H2O: Calculated: C, 60.88; H, 5.55, N, 4.90; Found: C, 61.09; H, 5.64; N, 4.73.

Workup

  1. customThe reaction product was not purified by chromatography

Sources & evidence

ORD record
ord-182de8fd71f7408a992cc2491650085a
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

Loading…