1,2,3,4-Tetrahydroisoquinoline → HCID 49850484, compound

HRID 403111Notes

Reaction equation

HRID 403111 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[CH2:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][NH:26]1.C(N(CC)CC)C>CC#N>[CH2:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][N:26]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 8471TriethylamineHCID 67128562HCID 67128562, compound

Product 1

HCID 49850484HCID 49850484, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound 2 (0.44 g, 1.13 mmol), 1,2,3,4-tetrahydroisoquinoline (0.22 g, 1.69 mmol) and triethylamine (0.218 g, 1.69 mmol) were added to 300 mL CH3CN, and the solution was stirred for two days. Purification was carried out on a silica gel TLC plate that was developed in 4% methanolic NH3 (7 M NH3 in methanol)/96% CH2Cl2. The product was obtained as pale yellow oil (73%). 1H NMR (CDCl3) δ 8.488 (dd, 1H, Ar), 7.616 (ddd, 1H, Ar), 7.573 (dd, 1H, Ar), 7.497 (dd, 1H, Ar), 7.219 (ddd, 1H, Ar), 7.090 (m, 4H, Ar), 7.004 (d, 1H, Ar), 6.933 (ddd, 1H, Ar), 6.833 (d, 1H, Ar), 3.789 (s, 3H, —OCH3), 3.766 (s, 2H, —CH2—), 3.671 (s, 2H, —CH2—), 3.608 (s, 2H, —CH2—), 2.895 (t, 2H, —CH2—), 2.712 (t, 2H, —CH2—), 2.491 (t, 2H, —CH2—), 2.455 (t, 2H, —CH2—), 1.554 (m, 4H, —CH2—CH2—), 1.298 (m, 4H, —CH2—CH2—). Mass Spec.=443.62 (M+H)+.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-7be73dacd3a64848b0c88804890d4b86
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

Loading…