N-(2-chloroethyl)perhydroazepine hydrochloride → 6-{2-[5-(2-Azepan-1-ylethoxy)-1,3-dihydroisoindol-2-yl]-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950292Notes

Reaction equation

HRID 1950292 reaction equation
COC1C=CC(C2CCC3C(=CC=C(OC)C=3)C2)=C(N2CC3C(=CC=C(O)C=3)C2)C=1.Cl.ClCCN1CCCCCC1.[N:42]1([CH2:49][CH2:50][O:51][C:52]2[CH:53]=[C:54]3[C:58](=[CH:59][CH:60]=2)[CH2:57][N:56]([C:61]2[CH:66]=[C:65]([O:67]C)[CH:64]=[CH:63][C:62]=2[CH:69]2[CH2:78][CH2:77][C:76]4[C:71](=[CH:72][CH:73]=[C:74]([O:79]C)[CH:75]=4)[CH2:70]2)[CH2:55]3)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>>[N:42]1([CH2:49][CH2:50][O:51][C:52]2[CH:53]=[C:54]3[C:58](=[CH:59][CH:60]=2)[CH2:57][N:56]([C:61]2[CH:66]=[C:65]([OH:67])[CH:64]=[CH:63][C:62]=2[CH:69]2[CH2:78][CH2:77][C:76]4[CH:75]=[C:74]([OH:79])[CH:73]=[CH:72][C:71]=4[CH2:70]2)[CH2:55]3)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1

Participants

4

Reactant 3

HCID 24188283N-(2-chloroethyl)perhydroazepine hydrochlorideHCID 579338902-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-2,3-dihydro-1H-isoindol-5-olHCID 697745255-(2-azepan-1-ylethoxy)-2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-2,3-dihydro-1H-isoindole

Product 1

HCID 579345586-{2-[5-(2-Azepan-1-ylethoxy)-1,3-dihydroisoindol-2-yl]-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 70.6%

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)azepane hydrochloride according to an analogous synthetic method to Preparation Example 40, 5-(2-azepan-1-ylethoxy)-2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-2,3-dihydro-1H-isoindole (223 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (149 mg).

Sources & evidence

ORD record
ord-780f16eb4024442bb94127269decd928
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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