Chloroform → HCID 21486984, compound

HRID 1414280Notes

Reaction equation

HRID 1414280 reaction equation
[CH:1]([N:4]([CH:8]([CH3:10])[CH3:9])[CH2:5][CH2:6][NH2:7])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(Cl)Cl.[CH3:22][O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][C:33]=1[O:34][CH3:35])[CH:30]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)[N:29]([C:44](Cl)=[O:45])[CH2:28][CH2:27]2>O>[CH:1]([N:4]([CH:8]([CH3:10])[CH3:9])[CH2:5][CH2:6][NH:7][C:44]([N:29]1[CH2:28][CH2:27][C:26]2[C:31](=[CH:32][C:33]([O:34][CH3:35])=[C:24]([O:23][CH3:22])[CH:25]=2)[CH:30]1[C:36]1[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=1)=[O:45])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 84591,2-Ethanediamine, N1,N1-bis(1-methylethyl)-HCID 8471TriethylamineHCID 21486950HCID 21486950, compound

Product 1

HCID 21486984HCID 21486984, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2.5 parts of 2-diisopropylaminoethylamine and 12 parts of triethylamine in approximately 225 parts of chloroform is added portionwise, at room temperature, a solution of 5.0 parts of 6,7-dimethoxy-1-(4-methoxyphenyl)-3,4-dihydro-2(1H)-isoquinolinecarbonyl chloride in about 75 parts of chloroform. The reaction mixture is stirred for 3 to 5 hours, allowed to stand overnight and then poured into water. The chloroform layer is separated, dried over anhydrous calcium sulfate and stripped of solvent under reduced pressure. The resultant oil is triturated with n-hexane to give a solid. Crystallization of that solid from ethyl ether affords N-(2-diisopropylaminoethyl)-6,7-dimethoxy-1-(4-methoxyphenyl)-3,4-dihydro-2(1H)-isoquinolinecarboxamide as a low melting solid. That compound is characterized by infrared absorption maxima in chloroform at about 1640 and 3400 cm-1.

Workup

  1. additionis added portionwise, at room temperature
  2. waitto stand overnight
  3. customThe chloroform layer is separated
  4. dry with materialdried over anhydrous calcium sulfate
  5. customThe resultant oil is triturated with n-hexane
  6. customto give a solid
  7. customCrystallization of that solid from ethyl ether

Sources & evidence

ORD record
ord-45db3c26e1964497b03dae51db50b780
Source dataset
uspto-grants-1977_01
Patent number
US04001244

Reaction notes

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