4-(2-Pyrrolidin-1-ylethoxy)benzoic acid hydrochloride → HCID 57934510, compound

HRID 1950259Notes

Reaction equation

HRID 1950259 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)CCCC1.[Si]([O:56][C:57]1[CH:58]=[CH:59][C:60]2[CH2:66][CH:65]([C:67]3[CH:72]=[CH:71][C:70]([O:73][CH3:74])=[CH:69][C:68]=3[N:75]([CH2:91][CH3:92])[CH2:76][C:77]3[CH:82]=[CH:81][C:80]([O:83][CH2:84][CH2:85][N:86]4[CH2:90][CH2:89][CH2:88][CH2:87]4)=[CH:79][CH:78]=3)[CH2:64][CH2:63][CH2:62][C:61]=2[CH:93]=1)(C(C)(C)C)(C)C>>[CH2:91]([N:75]([CH2:76][C:77]1[CH:82]=[CH:81][C:80]([O:83][CH2:84][CH2:85][N:86]2[CH2:87][CH2:88][CH2:89][CH2:90]2)=[CH:79][CH:78]=1)[C:68]1[CH:69]=[C:70]([O:73][CH3:74])[CH:71]=[CH:72][C:67]=1[CH:65]1[CH2:64][CH2:63][CH2:62][C:61]2[CH:93]=[C:57]([OH:56])[CH:58]=[CH:59][C:60]=2[CH2:66]1)[CH3:92]

Participants

4

Reactant 3

HCID 131748684-(2-Pyrrolidin-1-ylethoxy)benzoic acid hydrochlorideHCID 66626847{2-[2-(tert-Butyldimethylsilyloxy)-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]-5-methoxyphenyl}ethylamineHCID 66627421HCID 66627421, compound

Product 1

HCID 57934510HCID 57934510, compoundYield 87.1%

Procedure

Synthesized from {2-[2-(tert-butyldimethylsilyloxy)-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]-5-methoxyphenyl}ethylamine and 4-(2-pyrrolidin-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-pyrrolidin-1-ylethoxy)benzyl]amine (484 mg) was used according to an analogous synthetic method to Example 325 described below to provide the title compound (345 mg).

Sources & evidence

ORD record
ord-029fb32441564257a0e200008a0b047f
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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