Potassium Carbonate → HCID 67527215, compound

HRID 1864675Notes

Reaction equation

Br[CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.Cl.[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[CH2:23][NH:22][CH2:21][CH2:20]2.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[CH2:23][N:22]([CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)[CH2:21][CH2:20]2

Participants

Conditions

Temperature: 80 °C

Procedure

6.9 g of the compound obtained in Step 1, 6.1 g of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride and 7.7 g of potassium carbonate were added to 80 ml of acetonitrile, and stirred at 80° C. for 14 hours. After washing with 250 ml of distilled water and with 300 ml of aqueous NaCl, the resulting organic layer was dried over MgSO4, filtrated, and distilled under a reduced pressure to obtain 5.3 g of 6,7-dimethoxy-2-[2-(4-nitro-phenylsulfanyl)-ethyl]-1,2,3,4-tetrahydro-isoquinoline. The compound was stirred with 3.4 g of Iron, 6.74 ml of 35% HCl and 35 ml of methanol under 1 atmospheric nitrogen atmosphere for 20 hours. The reaction mixture was filtrated through a cellite pad, the pad was washed with methanol, and the filtrate and wash solution were combined, and distilled under a reduced pressure to obtain a residue that gave 3.0 g of the title compound (yield 33%).

Workup

washAfter washing with 250 ml of distilled water and with 300 ml of aqueous NaCl
dry with materialthe resulting organic layer was dried over MgSO4
filtrationfiltrated
distillationdistilled under a reduced pressure

Sources & evidence

ORD record: ord-68d86f9811204de39b884c3f1dd36e06
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625926B2

Reaction notes

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