HCID 2994469, compound → HCID 23087099, compound

HRID 1434445Notes

Reaction equation

HRID 1434445 reaction equation
N1(CCOC2C=CC(C#N)=CC=2)CCCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].N1(CCOC2C=CC(CN)=CC=2)CCCCC1.FC(F)(F)S(OC1C=C(OC)C=CC=1CC1CCC2C(=CC=C(OC)C=2)C1)(=O)=O.C[O:71][C:72]1[CH:73]=[CH:74][C:75]([CH2:95][CH:96]2[CH2:105][CH2:104][C:103]3[C:98](=[CH:99][CH:100]=[C:101]([O:106]C)[CH:102]=3)[CH2:97]2)=[C:76]([NH:78][CH2:79][C:80]2[CH:85]=[CH:84][C:83]([O:86][CH2:87][CH2:88][N:89]3[CH2:94][CH2:93][CH2:92][CH2:91][CH2:90]3)=[CH:82][CH:81]=2)[CH:77]=1>>[OH:71][C:72]1[CH:73]=[CH:74][C:75]([CH2:95][CH:96]2[CH2:105][CH2:104][C:103]3[CH:102]=[C:101]([OH:106])[CH:100]=[CH:99][C:98]=3[CH2:97]2)=[C:76]([NH:78][CH2:79][C:80]2[CH:81]=[CH:82][C:83]([O:86][CH2:87][CH2:88][N:89]3[CH2:90][CH2:91][CH2:92][CH2:93][CH2:94]3)=[CH:84][CH:85]=2)[CH:77]=1

Participants

6

Reactant 5

HCID 2994469HCID 2994469, compoundHCID 14425930HCID 14425930, compoundHCID 21226445Aluminium lithium hydrideHCID 23087515HCID 23087515, compoundHCID 66627615HCID 66627615, compound

Product 1

HCID 23087099HCID 23087099, compoundYield 68.7%

Procedure

Obtained by reducing 4-(2-piperidin-1-ylethoxy)benzonitrile with lithium aluminum hydride, 4-(2-piperidin-1-ylethoxy)benzylamine (350 mg) and 5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-ylmethyl)phenyl trifluoromethanesulfonate (1.0 g) were used according to an analogous synthetic method to Example 116 to synthesize [5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-ylmethyl)phenyl][4-(2-piperidin-1-ylethoxy)benzyl]amine (400 mg), which was used according to an analogous synthetic method to Example 111 to provide the title compound (260 mg).

Workup

  1. customObtained

Sources & evidence

ORD record
ord-6f822a1633144edf88c742a385fcfd94
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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