Diisopropylethylamine → 1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[7-phenyl-7-(phenylthio)heptyl]isoquinoline

HRID 863914Notes

Reaction equation

HRID 863914 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[CH2:10][NH:9][CH2:8][CH2:7]2.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([S:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(C(C)C)C(C)C)C>C(#N)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[CH2:10][N:9]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[S:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 64560356,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 10570687[(7-Bromo-1-phenylheptyl)thio]benzene

Product 1

HCID 106722321,2,3,4-Tetrahydro-6,7-dimethoxy-2-[7-phenyl-7-(phenylthio)heptyl]isoquinolineYield 36.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The free base from 4.60 g of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride, 3.63 g of [(7-bromo-1-phenylheptyl)thio]benzene, 50 ml of acetonitrile and 2.61 ml of ethyl diisopropylamine is heated at reflux temperature for 29 hours. The solvent is evaporated over night and the residue is partitioned between chloroform and aqueous ammonium hydroxide. The organic layer is dried and concentrated in vacuo to give 5.81 g of crude product. The residue is purified by chromatography (silica gel: chloroform/methyl alcohol) to give 1.73 g of the desired product. Calcd for C30H37NO2S: C=75.75: H=7.84; N=2.94; S=6.74 Found C=75.40; H=7.56; N=2.74; S=6.96 MS(CI): m/z 476(M-H+).

Workup

  1. temperatureat reflux temperature for 29 hours
  2. customThe solvent is evaporated over night
  3. customthe residue is partitioned between chloroform and aqueous ammonium hydroxide
  4. customThe organic layer is dried
  5. concentrationconcentrated in vacuo
  6. customto give 5.81 g of crude product
  7. customThe residue is purified by chromatography (silica gel: chloroform/methyl alcohol)

Sources & evidence

ORD record
ord-ceebc9d9acd44a8ebc5b8241ea073515
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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