2-(Piperidin-4-yl)phenol → HCID 67713164, compound

HRID 2256053Notes

Reaction equation

HRID 2256053 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]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]>O>[ClH:14].[Cl:14][C:15]1[CH:16]=[C:17]([C@H:22]([CH2:34][CH2:35][N:11]2[CH2:10][CH2:9][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[OH:1])[CH2:13][CH2:12]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

4

Reactant 2

HCID 107024522-(Piperidin-4-yl)phenolHCID 15381108(S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide

Product 1

HCID 67713164HCID 67713164, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using a procedure similar to that described in Example 1 (alternative preparation), except using 4-(2-hydroxyphenyl)piperidine and (S)-N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-methylbenzamide, the title compound was prepared. Chromatography, eluting with dichloromethane:methanol, followed by conversion to the hydrochloride salt gave a white solid; mp 205°-210° C.; MS: 511; NMR (CD3OD): 1.7-2.3 (m, 6), 2.7 (s, 1), 2.8-3.1 (m, 6), 3.2-3.8 (m, 5), 6.7-6.8 (m, 2), 7.0 (t, J=7, 3), 7.2 (br, 2), 7.4 (br, 2), 7.4 (br, 4), 7.5-7.7 (m, 2), 9.5 (s, 10), 10.5 (s, 1). Analysis for C29H32Cl2N2O2 ·1.0 HCl·0.75 H2O: Calculated: C, 62.04; H, 6.19; N, 4.99; Found: C, 62.24; H, 6.15; N, 5.08.

Workup

  1. customthat described in Example 1 (alternative preparation)
  2. washChromatography, eluting with dichloromethane
  3. customgave a white solid

Sources & evidence

ORD record
ord-7f0385b3475d4e98a5c00663efeae1cd
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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