N-(2-chloroethyl)perhydroazepine hydrochloride → 1-{2-{4-[5-Methoxy-2-(6-methoxynaphthalen-2-yl)benzyl]phenoxy}ethyl}azepane

HRID 1950028Notes

Reaction equation

HRID 1950028 reaction equation
OC1C=CC(C(C2C=C(OC)C=CC=2C2C=CC3C(=CC=C(OC)C=3)C=2)=O)=CC=1.Cl.ClCCN1CCCCCC1.[N:41]1([CH2:48][CH2:49][O:50][C:51]2[CH:56]=[CH:55][C:54]([C:57]([C:59]3[CH:64]=[C:63]([O:65][CH3:66])[CH:62]=[CH:61][C:60]=3[C:67]3[CH:76]=[CH:75][C:74]4[C:69](=[CH:70][CH:71]=[C:72]([O:77][CH3:78])[CH:73]=4)[CH:68]=3)=O)=[CH:53][CH:52]=2)[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1>>[CH3:66][O:65][C:63]1[CH:62]=[CH:61][C:60]([C:67]2[CH:76]=[CH:75][C:74]3[C:69](=[CH:70][CH:71]=[C:72]([O:77][CH3:78])[CH:73]=3)[CH:68]=2)=[C:59]([CH:64]=1)[CH2:57][C:54]1[CH:55]=[CH:56][C:51]([O:50][CH2:49][CH2:48][N:41]2[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]2)=[CH:52][CH:53]=1

Participants

4

Reactant 3

HCID 24188283N-(2-chloroethyl)perhydroazepine hydrochlorideHCID 57933864(4-Hydroxyphenyl)[5-methoxy-2-(6-methoxynaphthalen-2-yl)phenyl]methanoneHCID 66626326[4-(2-Azepan-1-ylethoxy)phenyl][5-methoxy-2-(6-methoxynaphthalen-2-yl)phenyl]methanone

Product 1

HCID 666277861-{2-{4-[5-Methoxy-2-(6-methoxynaphthalen-2-yl)benzyl]phenoxy}ethyl}azepaneYield 72%

Procedure

Synthesized from (4-hydroxyphenyl)[5-methoxy-2-(6-methoxynaphthalen-2-yl)phenyl]methanone and 1-(2-chloroethyl)azepane hydrochloride according to an analogous synthetic method to Preparation Example 40, [4-(2-azepan-1-ylethoxy)phenyl][5-methoxy-2-(6-methoxynaphthalen-2-yl)phenyl]methanone (1.0 g) was used according to an analogous synthetic method to Example 337 described below to provide 1-{2-{4-[5-methoxy-2-(6-methoxynaphthalen-2-yl)benzyl]phenoxy}ethyl}azepane (700 mg). This compound (421 mg) was used according to an analogous synthetic method to Example 111 described below to provide the title compound (105 mg).

Sources & evidence

ORD record
ord-fb43e3a5b60c4025a729a8d10beb96fd
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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