3-(Piperidin-4-yl)pyridine → (3R)-3-[(1S)-1-(3,4-Dichlorophenyl)-3-(4-pyrid-3-ylpiperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride

HRID 725118Notes

Reaction equation

HRID 725118 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([C@@H: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].[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:25]=1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([C@@H: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:33]2[CH2:34][CH2:35][CH:30]([C:26]3[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=3)[CH2:31][CH2:32]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 46903903-(Piperidin-4-yl)pyridineHCID 57040947(3S)-3-(3,4-Dichlorophenyl)-3-((1R)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde

Product 1

HCID 70113750(3R)-3-[(1S)-1-(3,4-Dichlorophenyl)-3-(4-pyrid-3-ylpiperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochlorideYield 164%

Procedure

A solution of (3S)-3-(3,4-dichlorophenyl)-3-((1R)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.428 g) was treated with 4-pyrid-3-ylpiperidine (0.20 g) as described in Example 8. The resulting material was not purified by chromatography, but was transformed into the hydrochloride to afford the title compound (0.535 g); [α]D =34° (c=1.0 ethanol); mp 170°-210° C. (dec); MS: m/z=494(M+1); NMR: 2.12 (m,4), 3.03 (s,3), 3.69 (m,7), 4.88 (m,1), 6.75 (m,1), 6.96 (m,1), 7.32 (m,1), 7.49 (m,2), 7.63(m,1), 7.92 (m,2), 8.37 (m,1), 8.81 (m,2). Analysis for C28H29Cl2N3O.2 HCl.H2O: Calculated C, 57.45; H, 5.68; N, 7.18; Found: C, 57.22; H, 5.67; N, 7.12.

Workup

  1. customThe resulting material was not purified by chromatography

Sources & evidence

ORD record
ord-d073eecb9a8d44e8b6d1dbcb5a0e4c93
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

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