Diisopropylethylamine → HCID 10697861, compound

HRID 1078792Notes

Reaction equation

HRID 1078792 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)([S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[C:8]#[N:9].Cl.[CH3:28][O:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][C:39]=1[O:40][CH3:41])[CH2:36][NH:35][CH2:34][CH2:33]2.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:26][O:25][C:19]1[CH:18]=[C:17]([C:7]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:35]2[CH2:34][CH2:33][C:32]3[C:37](=[CH:38][C:39]([O:40][CH3:41])=[C:30]([O:29][CH3:28])[CH:31]=3)[CH2:36]2)[C:8]#[N:9])[CH:22]=[CH:21][C:20]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 64560356,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 10812778HCID 10812778, compound

Product 1

HCID 10697861HCID 10697861, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture, under argon, of 1.5 g of product from Example 118, 0.790 g of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride, 7 ml of N,N-diisopropyl ethylamine and 60 ml of acetonitrile is heated at reflux temperature overnight. The reaction is cooled and concentrated in vacuo to give an oil. The oil is purified by chromatography (silica gel: 1 and 2% methyl alcohol/methylene chloride) to give 1.1 g of the desired product as a glassy yellow solid.

Workup

  1. temperatureat reflux temperature overnight
  2. temperatureThe reaction is cooled
  3. concentrationconcentrated in vacuo
  4. customto give an oil
  5. customThe oil is purified by chromatography (silica gel: 1 and 2% methyl alcohol/methylene chloride)

Sources & evidence

ORD record
ord-11b173dbaf844b47b6f015a65e9f0f37
Source dataset
uspto-grants-1996_08
Patent number
US05550149

Reaction notes

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