4-(2-(Methylsulfonyl)phenyl)piperidine → (3R)-3-[(1S)-1-(3,4-Dichlorophenyl)-3-(4-(2-methylsulfonylphenyl)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride

HRID 725108Notes

Reaction equation

HRID 725108 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].[CH3:24][S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)(=[O:27])=[O:26]>CO>[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:37]2[CH2:38][CH2:39][CH:34]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[S:25]([CH3:24])(=[O:27])=[O:26])[CH2:35][CH2:36]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 224526684-(2-(Methylsulfonyl)phenyl)piperidineHCID 57040947(3S)-3-(3,4-Dichlorophenyl)-3-((1R)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde

Product 1

HCID 70109087(3R)-3-[(1S)-1-(3,4-Dichlorophenyl)-3-(4-(2-methylsulfonylphenyl)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochlorideYield 124.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3S)-3-(3,4-Dichlorophenyl)-3-((1R)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.468 g) in methanol (10 mL) was treated with 4-(2-methylsulfonylphenyl)piperidine (0.3 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 =21° (c=1.0 Ethanol); mp 190°-200° C. (dec); MS: m/z=571(M+1); NMR(CD3SOCD3): 1.99 (broad,2), 2.37 (broad,2), 3.35 (s,3), 3.60 (s,3), 4.9 (d,1, J=3.6), 6.8 (dd,1, J=8.4, 2), 7.0 (s,1), 7.3-7.98 (m,9). Analysis for C30H32Cl2N2O2S.HCl.H2O: Calculated: C, 57.55; H, 5.63; N, 4.47; Found: C, 57.32; H, 5.33; N, 4.50.

Workup

  1. customThe resulting material was not purified by chromatography

Sources & evidence

ORD record
ord-e23a70e3e4334cd69cdaa96900ce0aad
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

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