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

HRID 725091Notes

Reaction equation

HRID 725091 reaction equation
[CH3:1][C:2]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)([CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[N:7]1[CH3:16])[CH2:3][CH:4]=O.[C:25]([NH:28][C:29]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)(=[O:27])[CH3:26]>>[ClH:23].[CH3:1][C:2]([CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[N:7]1[CH3:16])([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)[CH2:3][CH2:4][N:32]1[CH2:31][CH2:30][C:29]([NH:28][C:25](=[O:27])[CH3:26])([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 15886675N-(4-Phenylpiperidin-4-yl)acetamideHCID 218398323-Methyl-3-(3,4-dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde

Product 1

HCID 218398353-[1-Methyl-1-(3,4-dichlorophenyl)-3-(4-acetamido-4-phenylpiperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochlorideYield 127.5%

Procedure

3-Methyl-3-(3,4-dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (isomer B prepared as described in Example 37 sub-part c. above) (0.52 g) was coupled to 4-acetamido-4-phenylpiperidine (0.36 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 the Example 8 to afford the title compound (0.55 g); mp 200°-228° C.; MS: m/z=564(M+1); NMR: 1.0 (s,3), 1.99 (s,1), 2.36 (m,2), 2.7 (m,2), 3.26 (s,3), 4.65 (s,1), 5.94 (d,1, J=7.7), 7.18-7.41 (m,9), 7.54 (d,1 J=8.3), 7.77 (d, J=7.5).

Workup

  1. customThe reaction product was purified by chromatography

Sources & evidence

ORD record
ord-a39458d64bdc4f3faa0911fed3567af0
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

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