6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline → N-(2-tert-butoxybenzyl)-6-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-N-(pyridin-2-ylmethyl)hexan-1-amine
Reaction equation
C(OC1C=CC=CC=1CN(CC1C=CC=CN=1)CCCCCCC1CCC(C2C=CC=CC=2OC)CC1)(C)(C)C.Br[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][N:48]([CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[O:63][C:64]([CH3:67])([CH3:66])[CH3:65])[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][N:51]=1.[CH3:68][O:69][C:70]1[CH:71]=[C:72]2[C:77](=[CH:78][C:79]=1[O:80][CH3:81])[CH2:76][NH:75][CH2:74][CH2:73]2>>[C:64]([O:63][C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][C:57]=1[CH2:56][N:48]([CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][N:51]=1)[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][N:75]1[CH2:74][CH2:73][C:72]2[C:77](=[CH:78][C:79]([O:80][CH3:81])=[C:70]([O:69][CH3:68])[CH:71]=2)[CH2:76]1)([CH3:67])([CH3:66])[CH3:65]Participants
Reactant 3
Product 1
Procedure
The same procedure as described for compound 11 was applied to starting material 10 (0.4 g, 0.92 mmol) and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (0.267 g, 1.38 mmol). Purification was carried out on a silica gel TLC plate that was developed in with a 4.5% methanolic NH3 (7 M NH3 in methanol/94.5% CH2Cl2. The product was isolated as pale yellow oil (99%). 1H NMR (CDCl3) δ 8.463 (dt, 1H, Ar), 7.574 (m, 3H, Ar), 7.082 (m, 2H, Ar), 6.996 (m, 2H, Ar), 6.552 (s, 1H, Ar), 6.486 (s, 1H, Ar), 3.797 (s, 3H, —OCH3), 3.792 (s, 3H, —OCH3), 3.723 (s, 2H, —CH2—), 3.646, (s, 2H, —CH2—), 3.504 (s, 2H, —CH2—), 2.784 (t, 2H, —CH2—), 2.655 (t, 2H, —CH2—), 2.430 (m, 4H, —CH2—CH2—), 1.521 (m, 4H, —CH2—CH2—), 1.333 (s, 9H, —C(CH3)3—), 1.264 (m, 4H, —CH2—CH2—). Mass Spec=546.37 (M+H)+.
Workup
- customPurification
Sources & evidence
- ORD record
- ord-192849415fd44bde85f5e13f1ba3812a
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08747810B2
Reaction notes
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