Diethylamine → HCID 86592042, compound

HRID 1785905Notes

Reaction equation

C(N(CC)C1C=C2C([C@H](N(C3C=CC(N(CC)CC)=CC=3)C(=O)C)C[C@H](C)N2C(=O)C2C=CC(N(C)C)=CC=2)=CC=1)C.[Cl:43][C:44]1[CH:49]=[CH:48][C:47]([N:50]([C@H:54]2[C:63]3[C:58](=[CH:59][C:60]([N:64]4[CH2:69][CH2:68]O[CH2:66][CH2:65]4)=[CH:61][CH:62]=3)[N:57]([C:70](=[O:80])[C:71]3[CH:76]=[CH:75][C:74]([N:77]([CH3:79])[CH3:78])=[CH:73][CH:72]=3)[C@@H:56]([CH3:81])[CH2:55]2)[C:51](=[O:53])[CH3:52])=[CH:46][CH:45]=1.C(NCC)C.N1CCOCC1>>[Cl:43][C:44]1[CH:45]=[CH:46][C:47]([N:50]([C@H:54]2[C:63]3[C:58](=[CH:59][C:60]([N:64]([CH2:65][CH3:66])[CH2:69][CH3:68])=[CH:61][CH:62]=3)[N:57]([C:70](=[O:80])[C:71]3[CH:72]=[CH:73][C:74]([N:77]([CH3:78])[CH3:79])=[CH:75][CH:76]=3)[C@@H:56]([CH3:81])[CH2:55]2)[C:51](=[O:53])[CH3:52])=[CH:48][CH:49]=1

Participants

Reactant 4

HCID 8021Diethylamine

HCID 8083Morpholine

HCID 86592043HCID 86592043, compound

HCID 86592044HCID 86592044, compound

Product 1

HCID 86592042HCID 86592042, compound

Procedure

(±)-Cis-N-[7-diethylamino-1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-(4-diethylamino-phenyl)-acetamide was made in the same way as (±)-cis-N-(4-chloro-phenyl)-N-[1-(4-dimethylamino-benzoyl)-2-methyl-7-morpholin-4-yl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide except diethylamine was substituted for morpholine. The reaction was non-selective and yielded (±)-cis-N-(4-chloro-phenyl)-N-[7-diethylamino-1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide in addition to the titled compound.

Sources & evidence

ORD record: ord-54ae29eb40e94ac4b695192d33829aa6
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504508B2

Reaction notes

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