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

HRID 1950246Notes

Reaction equation

HRID 1950246 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C@@H:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([O:20]C(=O)C(C)(C)C)[CH:14]=[CH:13][C:12]=2[CH2:11]1)[CH3:2].[CH3:27][N:28]1[CH2:33][CH2:32][CH:31]([O:34][C:35]2[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=2)[CH2:30][CH2:29]1>>[CH2:1]([N:3]([CH2:39][C:38]1[CH:41]=[CH:42][C:35]([O:34][CH:31]2[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]2)=[CH:36][CH:37]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C@@H:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13][C:12]=2[CH2:11]1)[CH3:2]

Participants

3

Reactant 2

HCID 234332974-(1-Methylpiperidin-4-yloxy)benzaldehydeHCID 57933894pivalic acid (R)-6-(2-ethylaminophenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 57934464(R)-6-{2-{Ethyl[4-(1-methylpiperidin-4-yloxy)benzyl]amino}phenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 59.7%

Procedure

Synthesized from pivalic acid (R)-6-(2-ethylaminophenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (30 mg) and 4-(1-methylpiperidin-4-yloxy)benzaldehyde (94 mg) according to an analogous synthetic method to Example 264 and purified by LC-MS, the title compound (24 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-7af10e1670d643e1a7c768860358c1eb
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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