Methanol → (S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(3-hydroxyphenyl)piperidino]butyl]-N-methylbenzamide hydrochloride

HRID 2256057Notes

Reaction equation

HRID 2256057 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=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].ClCCl.CO>O>[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:4]3[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=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

6

Reactant 4

HCID 887Methanol2×HCID 6344DichloromethaneHCID 105834534-(3-Hydroxyphenyl)piperidineHCID 15381108(S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide

Product 1

HCID 67713199(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(3-hydroxyphenyl)piperidino]butyl]-N-methylbenzamide hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using a procedure similar to that described in Example 1 (alternative preparation), except using 4-(3-hydroxyphenyl)piperidine and (S)-N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-methylbenzamide, the title compound was prepared. Chromatography with dichloromethane:methanol followed by conversion to the hydrochloride salt gave a white solid; mp 178°-182° C.; MS: 511; NMR (CD3OD): 1.8-2.3 (m, 6), 2.8 (s, 3), 2.8-3.3 (m, 6), 3.4-3.9 (m, 4), 6.6-6.7 (m, 3), 7.0 (d, J=7, 1), 7.1-7.2 (m, 3), 7.3-7.6 (m, 6); [α]D =-40.3°, c=0.645 (methanol). Analysis for C29H2Cl2N2O2 ·1.0 HCl·0.5 H2O: Calculated: C, 62.54; H, 6.15; N, 5.03; Found: C, 62.19; H, 6.10; N, 5.0.

Workup

  1. customthat described in Example 1 (alternative preparation)
  2. customgave a white solid

Sources & evidence

ORD record
ord-c35df4847a744889aff19a5d7b7417c5
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

Loading…