Piperidine, 1-(2-chloroethyl)-, hydrochloride → 6-{2-{Cyclopropylmethyl {2-[4-(2-piperidin-1-ylethoxy)phenyl]ethyl}amino}-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950342Notes

Reaction equation

HRID 1950342 reaction equation
C1(CN(C2C=C(OC)C=CC=2C2CCC3C(=CC=C(OC)C=3)C2)CCC2C=CC(O)=CC=2)CC1.Cl.ClCCN1CCCCC1.[CH:45]1([CH2:48][N:49]([C:67]2[CH:72]=[C:71]([O:73]C)[CH:70]=[CH:69][C:68]=2[CH:75]2[CH2:84][CH2:83][C:82]3[C:77](=[CH:78][CH:79]=[C:80]([O:85]C)[CH:81]=3)[CH2:76]2)[CH2:50][CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH2:60][N:61]3[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]3)=[CH:54][CH:53]=2)[CH2:47][CH2:46]1>>[CH:45]1([CH2:48][N:49]([CH2:50][CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH2:60][N:61]3[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]3)=[CH:54][CH:53]=2)[C:67]2[CH:72]=[C:71]([OH:73])[CH:70]=[CH:69][C:68]=2[CH:75]2[CH2:84][CH2:83][C:82]3[CH:81]=[C:80]([OH:85])[CH:79]=[CH:78][C:77]=3[CH2:76]2)[CH2:47][CH2:46]1

Participants

4

Reactant 3

HCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 230875484-{2-{Cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amino}ethyl}phenolHCID 66626358Cyclopropylmethyl [5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]{2-[4-(2-piperidin-1-ylethoxy)phenyl]ethyl}amine

Product 1

HCID 579339536-{2-{Cyclopropylmethyl {2-[4-(2-piperidin-1-ylethoxy)phenyl]ethyl}amino}-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 47.6%

Procedure

Synthesized from 4-{2-{cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amino}ethyl}phenol and 1-(2-chloroethyl)piperidine hydrochloride according to an analogous synthetic method to Preparation Example 40, cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]{2-[4-(2-piperidin-1-ylethoxy)phenyl]ethyl}amine (351 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (159 mg).

Sources & evidence

ORD record
ord-65b0059a3cf54ae1ad065f8083e67ea7
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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