4-(2-Azepan-1-ylethoxy)benzoic acid hydrochloride → [4-(2-Azepan-1-ylethoxy)benzyl]ethyl[5-methoxy-2-(6-methoxy-3,3-dimethyl-3,4-dihydronaphthalen-2-yl)phenyl]amine

HRID 1950268Notes

Reaction equation

HRID 1950268 reaction equation
COC1C=CC(C2C(C)(C)CC3C(=CC=C(OC)C=3)C=2)=C(N)C=1.Cl.[N:25]1([CH2:32][CH2:33][O:34][C:35]2[CH:43]=[CH:42][C:38]([C:39](O)=O)=[CH:37][CH:36]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.N1(CCOC2C=C[C:57]([CH2:58][NH:59][C:60]3[CH:65]=[C:64]([O:66][CH3:67])[CH:63]=[CH:62][C:61]=3[C:68]3[C:77]([CH3:79])([CH3:78])[CH2:76][C:75]4[C:70](=[CH:71][CH:72]=[C:73]([O:80][CH3:81])[CH:74]=4)[CH:69]=3)=CC=2)CCCCCC1>>[N:25]1([CH2:32][CH2:33][O:34][C:35]2[CH:43]=[CH:42][C:38]([CH2:39][N:59]([CH2:58][CH3:57])[C:60]3[CH:65]=[C:64]([O:66][CH3:67])[CH:63]=[CH:62][C:61]=3[C:68]3[C:77]([CH3:79])([CH3:78])[CH2:76][C:75]4[C:70](=[CH:71][CH:72]=[C:73]([O:80][CH3:81])[CH:74]=4)[CH:69]=3)=[CH:37][CH:36]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 3

HCID 131748704-(2-Azepan-1-ylethoxy)benzoic acid hydrochlorideHCID 230873205-Methoxy-2-(6-methoxy-3,3-dimethyl-3,4-dihydronaphthalen-2-yl)phenylamineHCID 66626307[4-(2-Azepan-1-ylethoxy)benzyl][5-methoxy-2-(6-methoxy-3,3-dimethyl-3,4-dihydronaphthalen-2-yl)phenyl]amine

Product 1

HCID 66626526[4-(2-Azepan-1-ylethoxy)benzyl]ethyl[5-methoxy-2-(6-methoxy-3,3-dimethyl-3,4-dihydronaphthalen-2-yl)phenyl]amine

Procedure

Synthesized from 5-methoxy-2-(6-methoxy-3,3-dimethyl-3,4-dihydronaphthalen-2-yl)phenylamine and 4-(2-azepan-1-ylethoxy)benzoic acid hydrochloride according to an analogous synthetic method to Example 152, [4-(2-azepan-1-ylethoxy)benzyl][5-methoxy-2-(6-methoxy-3,3-dimethyl-3,4-dihydronaphthalen-2-yl)phenyl]amine (454 mg) was used according to an analogous synthetic method to Example 36 to provide [4-(2-azepan-1-ylethoxy)benzyl]ethyl[5-methoxy-2-(6-methoxy-3,3-dimethyl-3,4-dihydronaphthalen-2-yl)phenyl]amine (387 mg). This compound (385 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (345 mg).

Sources & evidence

ORD record
ord-6ddedaf5e666485f85c6eb7085897a0e
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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