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

HRID 1950185Notes

Reaction equation

HRID 1950185 reaction equation
C(NC1C=C(OC)C=CC=1C1CCC2C=C(OC(=O)C(C)(C)C)C=CC=2C1)C.CN1CCC(OC2C=CC(C=O)=CC=2)CC1.[CH2:45]([N:47]([CH2:73][C:74]1[CH:79]=[CH:78][C:77]([O:80][CH:81]2[CH2:86][CH2:85][N:84]([CH3:87])[CH2:83][CH2:82]2)=[CH:76][CH:75]=1)[C:48]1[CH:53]=[C:52]([O:54][CH3:55])[CH:51]=[CH:50][C:49]=1[CH:56]1[CH2:65][CH2:64][C:63]2[CH:62]=[C:61]([O:66]C(=O)C(C)(C)C)[CH:60]=[CH:59][C:58]=2[CH2:57]1)[CH3:46]>>[CH2:45]([N:47]([CH2:73][C:74]1[CH:75]=[CH:76][C:77]([O:80][CH:81]2[CH2:86][CH2:85][N:84]([CH3:87])[CH2:83][CH2:82]2)=[CH:78][CH:79]=1)[C:48]1[CH:53]=[C:52]([O:54][CH3:55])[CH:51]=[CH:50][C:49]=1[CH:56]1[CH2:65][CH2:64][C:63]2[CH:62]=[C:61]([OH:66])[CH:60]=[CH:59][C:58]=2[CH2:57]1)[CH3:46]

Participants

4

Reactant 3

HCID 234332974-(1-Methylpiperidin-4-yloxy)benzaldehydeHCID 579340956-(2-(Ethylamino)-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl pivalateHCID 66625867Pivalic acid 6-{2-{ethyl[4-(1-methylpiperidin-4-yloxy)benzyl]amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 579337666-{2-{Ethyl[4-(1-methylpiperidin-4-yloxy)benzyl]amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 61.7%

Procedure

Synthesized from pivalic acid 6-(2-ethylamino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester and 4-(1-methylpiperidin-4-yloxy)benzaldehyde according to an analogous synthetic method to Example 212, pivalic acid 6-{2-{ethyl[4-(1-methylpiperidin-4-yloxy)benzyl]amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (70 mg) was used according to an analogous synthetic method to Example 217 to provide the title compound (37 mg).

Sources & evidence

ORD record
ord-fa62dbafc1464bab9061e414ba7ec49f
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

Loading…