N-(4-Phenylpiperidin-4-yl)acetamide → 3-[1-(3,4-Dichlorophenyl)-3-(4-acetamido-4-Phenylpiperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride

HRID 725068Notes

Reaction equation

HRID 725068 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:24]([NH:27][C:28]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)(=[O:26])[CH3:25]>>[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:31]2[CH2:32][CH2:33][C:28]([NH:27][C:24](=[O:26])[CH3:25])([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:29][CH2:30]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 15886675N-(4-Phenylpiperidin-4-yl)acetamideHCID 218397793-(3,4-dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde

Product 1

HCID 218397703-[1-(3,4-Dichlorophenyl)-3-(4-acetamido-4-Phenylpiperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochlorideYield 83.2%

Procedure

3-(3,4-Dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.375 g) was coupled to 4-acetamido-4-phenylpiperidine (0.28 g) by a method similar to that described in Example 8. The reaction product was purified by chromatography and converted to the corresponding hydrochloride salt as described in Example 8 to afford the title compound (0.263 g); mp 185°-192° C.; MS: m/z=550(M+1); NMR(CD3 SOCD3): 1.91 (s,3), 2.3 (m,2), 3.06 (s,3), 3.15 (m,2), 4.87 (d,1, J=3.5), 6.8 (d,1, J=8), 7.0 (d,1, J=1.8), 7.23 (m,1), 7.34 (m,5), 7.48 (m,2), 7.65 (m,1), 7.90 (d,1, J=7.6), 8.1 (s,1). Analysis for C31 H33Cl2N3O2.1.5 HCl: Calculated: C, 60.64; H, 6.07; N, 6.84; Found: C, 60.98; H, 5.91; N, 6.75.

Workup

  1. customThe reaction product was purified by chromatography

Sources & evidence

ORD record
ord-10f3620e80a54f8aa736ceaadcb666b1
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

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