4-(1-Methylpiperidin-4-yloxy)benzaldehyde → (R)-6-{2-{Ethyl[4-(1-methylpiperidin-4-yloxy)benzyl]amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 2423768Notes

Reaction equation

HRID 2423768 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[C@@H:12]1[CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([O:22]C(=O)C(C)(C)C)[CH:16]=[CH:15][C:14]=2[CH2:13]1)[CH3:2].[CH3:29][N:30]1[CH2:35][CH2:34][CH:33]([O:36][C:37]2[CH:44]=[CH:43][C:40]([CH:41]=O)=[CH:39][CH:38]=2)[CH2:32][CH2:31]1>>[CH2:1]([N:3]([CH2:41][C:40]1[CH:39]=[CH:38][C:37]([O:36][CH:33]2[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]2)=[CH:44][CH:43]=1)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[C@@H:12]1[CH2:21][CH2:20][C:15]2[CH:16]=[C:17]([OH:22])[CH:18]=[CH:19][C:14]=2[CH2:13]1)[CH3:2]

Participants

3

Reactant 2

HCID 234332974-(1-Methylpiperidin-4-yloxy)benzaldehydeHCID 57934253HCID 57934253, compound

Product 1

HCID 57934546(R)-6-{2-{Ethyl[4-(1-methylpiperidin-4-yloxy)benzyl]amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 71.6%

Procedure

Synthesized from pivalic acid (R)-6-(2-ethylamino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (33 mg) and 4-(1-methylpiperidin-4-yloxy)benzaldehyde (94 mg) according to an analogous synthetic method to Example 264 described below and purified by LC-MS, the title compound (31 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-4f27506c45844d20b04ed078541ae810
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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