7-Methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine → 7-methoxy-3-{5-methoxy-2-[4-(2-piperidin-1-ylethoxy)benzyl]phenyl)-2,3,4,5-tetrahydro-1H-benz[d]azepine

HRID 1433852Notes

Reaction equation

HRID 1433852 reaction equation
COC1C=CC2CCNCCC=2C=1.BrC1C=C(OC)C=CC=1C(C1C=CC(OCCN2CCCCC2)=CC=1)=O.[CH3:40][O:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]([C:50]2[CH:55]=[CH:54][C:53]([O:56][CH2:57][CH2:58][N:59]3[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60]3)=[CH:52][CH:51]=2)=O)=[C:44]([N:65]2[CH2:71][CH2:70][C:69]3[CH:72]=[C:73]([O:76][CH3:77])[CH:74]=[CH:75][C:68]=3[CH2:67][CH2:66]2)[CH:43]=1>>[CH3:77][O:76][C:73]1[CH:74]=[CH:75][C:68]2[CH2:67][CH2:66][N:65]([C:44]3[CH:43]=[C:42]([O:41][CH3:40])[CH:47]=[CH:46][C:45]=3[CH2:48][C:50]3[CH:55]=[CH:54][C:53]([O:56][CH2:57][CH2:58][N:59]4[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64]4)=[CH:52][CH:51]=3)[CH2:71][CH2:70][C:69]=2[CH:72]=1

Participants

4

Reactant 3

HCID 138533487-Methoxy-2,3,4,5-tetrahydro-1h-3-benzazepineHCID 23087562[4-Methoxy-2-(7-methoxy-1,2,4,5-tetrahydrobenz[d]azepin-3-yl)phenyl][4-(2-piperidin-1-ylethoxy)phenyl]methanoneHCID 57933784(2-Bromo-4-methoxyphenyl)[4-(2-piperidin-1-ylethoxy)phenyl]methanone

Product 1

HCID 666270427-methoxy-3-{5-methoxy-2-[4-(2-piperidin-1-ylethoxy)benzyl]phenyl)-2,3,4,5-tetrahydro-1H-benz[d]azepineYield 83.6%

Procedure

Synthesized from 7-methoxy-2,3,4,5-tetrahydro-1H-benz[d]azepine and (2-bromo-4-methoxyphenyl)[4-(2-piperidin-1-ylethoxy)phenyl]methanone according to an analogous synthetic method to Example 116 described below, [4-methoxy-2-(7-methoxy-1,2,4,5-tetrahydrobenz[d]azepin-3-yl)phenyl][4-(2-piperidin-1-ylethoxy)phenyl]methanone (632 mg) was used according to an analogous synthetic method to Example 337 described below to provide 7-methoxy-3-{5-methoxy-2-[4-(2-piperidin-1-ylethoxy)benzyl]phenyl}-2,3,4,5-tetrahydro-1H-benz[d]azepine (514 mg). The total amount of this compound was used according to an analogous synthetic method to Example 111 described below to provide the title compound (355 mg).

Sources & evidence

ORD record
ord-2896846ceab24a06aeb249e4185b6b67
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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