4-(2-Piperidinoethoxy)benzoic acid hydrochloride → 6-{2-{Ethyl[4-(2-piperidin-1-ylethoxy)benzyl]amino}-4-methoxyphenyl}-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol

HRID 1950260Notes

Reaction equation

HRID 1950260 reaction equation
[Si](OC1C=CC2CC(C3C=CC(OC)=CC=3CCN)CCCC=2C=1)(C(C)(C)C)(C)C.Cl.N1(CCOC2C=CC(C(O)=O)=CC=2)CCCCC1.[Si]([O:57][C:58]1[CH:59]=[CH:60][C:61]2[CH2:67][CH:66]([C:68]3[CH:73]=[CH:72][C:71]([O:74][CH3:75])=[CH:70][C:69]=3[N:76]([CH2:93][CH3:94])[CH2:77][C:78]3[CH:83]=[CH:82][C:81]([O:84][CH2:85][CH2:86][N:87]4[CH2:92][CH2:91][CH2:90][CH2:89][CH2:88]4)=[CH:80][CH:79]=3)[CH2:65][CH2:64][CH2:63][C:62]=2[CH:95]=1)(C(C)(C)C)(C)C>>[CH2:93]([N:76]([CH2:77][C:78]1[CH:83]=[CH:82][C:81]([O:84][CH2:85][CH2:86][N:87]2[CH2:92][CH2:91][CH2:90][CH2:89][CH2:88]2)=[CH:80][CH:79]=1)[C:69]1[CH:70]=[C:71]([O:74][CH3:75])[CH:72]=[CH:73][C:68]=1[CH:66]1[CH2:65][CH2:64][CH2:63][C:62]2[CH:95]=[C:58]([OH:57])[CH:59]=[CH:60][C:61]=2[CH2:67]1)[CH3:94]

Participants

4

Reactant 3

HCID 57438354-(2-Piperidinoethoxy)benzoic acid hydrochlorideHCID 66626261{2-[2-(tert-butyldimethylsilyloxy)-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]-5-methoxyphenyl}ethyl[4-(2-piperidin-1-ylethoxy)benzyl]amineHCID 66626847{2-[2-(tert-Butyldimethylsilyloxy)-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]-5-methoxyphenyl}ethylamine

Product 1

HCID 579340476-{2-{Ethyl[4-(2-piperidin-1-ylethoxy)benzyl]amino}-4-methoxyphenyl}-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-olYield 90.3%

Procedure

Synthesized from {2-[2-(tert-butyldimethylsilyloxy)-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]-5-methoxyphenyl}ethylamine and 4-(2-piperidin-1-ylethoxy)benzoic acid hydrochloride according to an analogous synthetic method to Example 152, {2-[2-(tert-butyldimethylsilyloxy)-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]-5-methoxyphenyl}ethyl[4-(2-piperidin-1-ylethoxy)benzyl]amine (481 mg) was used according to an analogous synthetic method to Example 325 described below to provide the title compound (357 mg).

Sources & evidence

ORD record
ord-0d310321c9674bf59d008949ab2d5890
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

Loading…