HCID 2994469, compound → HCID 23087116, compound

HRID 1434443Notes

Reaction equation

HRID 1434443 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].N1(CCOC2C=CC(CN)=CC=2)CCCCC1.FC(F)(F)S(O[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[CH2:53][CH:54]1[CH2:63][CH2:62][C:61]2[C:56](=[CH:57][CH:58]=[C:59]([O:64][CH3:65])[CH:60]=2)[CH2:55]1)(=O)=O>>[CH3:65][O:64][C:59]1[CH:60]=[C:61]2[C:56](=[CH:57][CH:58]=1)[CH2:55][CH:54]([CH2:53][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=1[NH:15][CH2:14][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:17][CH:16]=1)[CH2:63][CH2:62]2

Participants

5

Reactant 4

HCID 2994469HCID 2994469, compoundHCID 14425930HCID 14425930, compoundHCID 21226445Aluminium lithium hydrideHCID 23087537HCID 23087537, compound

Product 1

HCID 23087116HCID 23087116, compound

Procedure

Obtained by reducing 4-(2-piperidin-1-ylethoxy)benzonitrile with lithium aluminum hydride, 4-(2-piperidin-1-ylethoxy)benzylamine (1.3 g) and 2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-ylmethyl)phenyl trifluoromethanesulfonate (1.4 g) were used according to an analogous synthetic method to Example 116 to provide [2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-ylmethyl)phenyl][4-(2-piperidin-1-ylethoxy)benzyl]amine (1.2 g). A portion thereof (200 mg) was used according to an analogous synthetic method to Example 364 to provide the title compound (100 mg).

Workup

  1. customObtained

Sources & evidence

ORD record
ord-459ec65efa93450697317519ca678e1e
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

Loading…