2-(6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-3-methylphenylamine → [4-(2-Azepan-1-ylethoxy)benzyl]ethyl[2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-3-methylphenyl]amine

HRID 1950250Notes

Reaction equation

HRID 1950250 reaction equation
COC1C=C2C(=CC=1)CC(C1C(C)=CC=CC=1N)CC2.Cl.[N:22]1([CH2:29][CH2:30][O:31][C:32]2[CH:40]=[CH:39][C:35]([C:36](Cl)=O)=[CH:34][CH:33]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.N1(CCOC2C=C[C:54]([CH2:55][NH:56][C:57]3[CH:62]=[CH:61][CH:60]=[C:59]([CH3:63])[C:58]=3[CH:64]3[CH2:73][CH2:72][C:71]4[C:66](=[CH:67][CH:68]=[C:69]([O:74][CH3:75])[CH:70]=4)[CH2:65]3)=CC=2)CCCCCC1>>[N:22]1([CH2:29][CH2:30][O:31][C:32]2[CH:40]=[CH:39][C:35]([CH2:36][N:56]([CH2:55][CH3:54])[C:57]3[CH:62]=[CH:61][CH:60]=[C:59]([CH3:63])[C:58]=3[CH:64]3[CH2:73][CH2:72][C:71]4[C:66](=[CH:67][CH:68]=[C:69]([O:74][CH3:75])[CH:70]=4)[CH2:65]3)=[CH:34][CH:33]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 3

HCID 230873752-(6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-3-methylphenylamineHCID 66627118[4-(2-Azepan-1-ylethoxy)benzyl][2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-3-methylphenyl]amineHCID 866052404-(2-Azepan-1-ylethoxy)benzoyl chloride hydrochloride

Product 1

HCID 66627430[4-(2-Azepan-1-ylethoxy)benzyl]ethyl[2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-3-methylphenyl]amine

Procedure

Synthesized from 2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-3-methylphenylamine and 4-(2-azepan-1-ylethoxy)benzoyl chloride hydrochloride according to an analogous synthetic method to Example 152, [4-(2-azepan-1-ylethoxy)benzyl][2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-3-methylphenyl]amine (565 mg) was used according to an analogous synthetic method to Example 36 to provide [4-(2-azepan-1-ylethoxy)benzyl]ethyl[2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-3-methylphenyl]amine (437 mg). This compound (435 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (253 mg).

Sources & evidence

ORD record
ord-61f71b54263d4c6689714badb0dc79a3
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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