(S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide → (S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(2-fluoropyrid-3-yl)piperidino]butyl]-N-methylbenzamide hydrochloride

HRID 2256065Notes

Reaction equation

HRID 2256065 reaction equation
[F:1][C:2]1[C:7]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:14][C:15]1[CH:16]=[C:17]([C@H:22]([CH2:34][CH:35]=O)[CH2:23][N:24]([CH3:33])[C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:18]=[CH:19][C:20]=1[Cl:21]>>[ClH:14].[Cl:14][C:15]1[CH:16]=[C:17]([C@H:22]([CH2:34][CH2:35][N:11]2[CH2:12][CH2:13][CH:8]([C:7]3[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=3)[CH2:9][CH2:10]2)[CH2:23][N:24]([CH3:33])[C:25](=[O:32])[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

3

Reactant 2

HCID 15381108(S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamideHCID 218397632-Fluoro-3-(piperidin-4-YL)pyridine

Product 1

HCID 67713056(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(2-fluoropyrid-3-yl)piperidino]butyl]-N-methylbenzamide hydrochloride

Procedure

Using a procedure similar to that described in Example 1 (alternative preparation), except using 4-(2-fluoropyrid-3-yl)piperidine and (S)-N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-methylbenzamide, the title compound was prepared. Conversion to the hydrochloride salt gave a white solid; mp 74°-95° C.; MS: 514; NMR (CD3OD): 1.9-2.3 (b, 6), 2.7-3.2 (m, 9), 3.4-3.9 (m, 4), 7.0-7.2 (m, 3), 7.3-7.4 (m, 5), 7.6 (m, 2), 7.8-7.9 (t, J=8, 1), 8.1 (d, J=4, 1). Analysis for C28H30Cl2FN3O·1.0 HCl·0.5 H2O: Calculated: C, 60.06; H, 5.76; N, 7.50. Found: C, 60.13; H, 6.06; N, 7.02.

Workup

  1. customthat described in Example 1 (alternative preparation)

Sources & evidence

ORD record
ord-0d4f96f43d4e4fa98557c8a7030dfeaf
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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