1-[2-(4-Bromophenoxy)ethyl]piperidine → 5-{4-Methoxy-2-[4-(2-piperidin-1-ylethoxy)phenylamino]phenyl}indan-1-ol

HRID 1950284Notes

Reaction equation

HRID 1950284 reaction equation
[Si](OC1C2C(=CC(C3C=CC(OC)=CC=3N)=CC=2)CC1)(C(C)(C)C)(C)C.BrC1C=CC(OCCN2CCCCC2)=CC=1.[Si]([O:50][CH:51]1[C:59]2[C:54](=[CH:55][C:56]([C:60]3[CH:65]=[CH:64][C:63]([O:66][CH3:67])=[CH:62][C:61]=3[NH:68][C:69]3[CH:74]=[CH:73][C:72]([O:75][CH2:76][CH2:77][N:78]4[CH2:83][CH2:82][CH2:81][CH2:80][CH2:79]4)=[CH:71][CH:70]=3)=[CH:57][CH:58]=2)[CH2:53][CH2:52]1)(C(C)(C)C)(C)C>>[CH3:67][O:66][C:63]1[CH:64]=[CH:65][C:60]([C:56]2[CH:55]=[C:54]3[C:59](=[CH:58][CH:57]=2)[CH:51]([OH:50])[CH2:52][CH2:53]3)=[C:61]([NH:68][C:69]2[CH:74]=[CH:73][C:72]([O:75][CH2:76][CH2:77][N:78]3[CH2:83][CH2:82][CH2:81][CH2:80][CH2:79]3)=[CH:71][CH:70]=2)[CH:62]=1

Participants

4

Reactant 3

HCID 8671951-[2-(4-Bromophenoxy)ethyl]piperidineHCID 579337352-[1-(Tert-butyldimethylsilyloxy)indan-5-yl]-5-methoxyphenylamineHCID 66626359{2-[1-(Tert-butyldimethylsilyloxy)indan-5-yl]-5-methoxyphenyl}[4-(2-piperidin-1-ylethoxy)phenyl]amine

Product 1

HCID 230872715-{4-Methoxy-2-[4-(2-piperidin-1-ylethoxy)phenylamino]phenyl}indan-1-olYield 69%

Procedure

Synthesized from 2-[1-(tert-butyldimethylsilyloxy)indan-5-yl]-5-methoxyphenylamine and 1-[2-(4-bromophenoxy)ethyl]piperidine according to an analogous synthetic method to Example 116, {2-[1-(tert-butyldimethylsilyloxy)indan-5-yl]-5-methoxyphenyl}[4-(2-piperidin-1-ylethoxy)phenyl]amine (1.1 g) was used according to an analogous synthetic method to Example 325 to provide the title compound (608 mg).

Sources & evidence

ORD record
ord-b28301d9e46f4f098ec886dc7ab8fd50
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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