[1,4'-Bipiperidin]-2-one → (3R)-3-[(1S)-1-(3,4-Dichlorophenyl)-3-(4-(2-oxo-piperidino)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride

HRID 1738976Notes

Reaction equation

HRID 1738976 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].[O:24]=[C:25]1[CH2:30][CH2:29][CH2:28][CH2:27][N:26]1[CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]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:34]2[CH2:33][CH2:32][CH:31]([N:26]3[CH2:27][CH2:28][CH2:29][CH2:30][C:25]3=[O:24])[CH2:36][CH2:35]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 21839852[1,4'-Bipiperidin]-2-oneHCID 57040947(3S)-3-(3,4-Dichlorophenyl)-3-((1R)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde

Product 1

HCID 70113899(3R)-3-[(1S)-1-(3,4-Dichlorophenyl)-3-(4-(2-oxo-piperidino)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochlorideYield 108.2%

Procedure

A solution of (3S)-3-(3,4-Dichlorophenyl)-3-((1R)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.596 g) was treated with 4-(2-oxopiperidino)piperidine (0.311 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 (0.51 g); [α]D =28° (c=1.0 Ethanol); mp 150-160° C. (dec); MS: m/z=514(M+1); NMR(CD3SOCD3): 1.69 (broad,5), 2.23 (broad, 3), 3.06 (s,3), 4.57 (m,1), 4.87 (d,1, J=3.7), 6.75 (dd,1, J=8.4, 2), 6.96 (d,1, J=2), 7.33 (d,1, J=8), 7.50 (m,2), 7.62 (m,1), 7.92 (d,1, J=7.6). Analysis for C28H33Cl2N3O2.1.5 HCl.H2O: Calculated: C, 57.27; H, 6.26; N, 7.16; Found: C, 57.24; H, 6.15; N, 7.26.

Workup

  1. customThe resulting material was not purified by chromatography

Sources & evidence

ORD record
ord-09a2c3e1c83d49b786eb16bcdef1b550
Source dataset
uspto-grants-1999_10
Patent number
US05965576

Reaction notes

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