Piperidine, 1-(2-chloroethyl)-, hydrochloride → 6-{4-Hydroxy-2-[5-(2-piperidin-1-ylethoxy)-1,3-dihydroisoindol-2-yl]phenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950291Notes

Reaction equation

HRID 1950291 reaction equation
COC1C=CC(C2CCC3C(=CC=C(OC)C=3)C2)=C(N2CC3C(=CC=C(O)C=3)C2)C=1.Cl.ClCCN1CCCCC1.C[O:42][C:43]1[CH:44]=[CH:45][C:46]([CH:67]2[CH2:76][CH2:75][C:74]3[C:69](=[CH:70][CH:71]=[C:72]([O:77]C)[CH:73]=3)[CH2:68]2)=[C:47]([N:49]2[CH2:57][C:56]3[C:51](=[CH:52][CH:53]=[C:54]([O:58][CH2:59][CH2:60][N:61]4[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]4)[CH:55]=3)[CH2:50]2)[CH:48]=1>>[OH:42][C:43]1[CH:44]=[CH:45][C:46]([CH:67]2[CH2:76][CH2:75][C:74]3[CH:73]=[C:72]([OH:77])[CH:71]=[CH:70][C:69]=3[CH2:68]2)=[C:47]([N:49]2[CH2:57][C:56]3[C:51](=[CH:52][CH:53]=[C:54]([O:58][CH2:59][CH2:60][N:61]4[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]4)[CH:55]=3)[CH2:50]2)[CH:48]=1

Participants

4

Reactant 3

HCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 579338902-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-2,3-dihydro-1H-isoindol-5-olHCID 697749672-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-5-(2-piperidin-1-ylethoxy)-2,3-dihydro-1H-isoindole

Product 1

HCID 579340766-{4-Hydroxy-2-[5-(2-piperidin-1-ylethoxy)-1,3-dihydroisoindol-2-yl]phenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 59.7%

Procedure

Synthesized from 2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-2,3-dihydro-1H-isoindol-5-ol and 1-(2-chloroethyl)piperidine hydrochloride according to an analogous synthetic method to Preparation Example 40, 2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-5-(2-piperidin-1-ylethoxy)-2,3-dihydro-1H-isoindole (218 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (123 mg).

Sources & evidence

ORD record
ord-ef2d16b8cb594e86be3f987448ef7301
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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