N,N-Diethylethylenediamine → HCID 21486957, compound

HRID 1414278Notes

Reaction equation

HRID 1414278 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[CH:17]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[N:16]([C:29](Cl)=[O:30])[CH2:15][CH2:14]2>O>[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH:6][C:29]([N:16]1[CH2:15][CH2:14][C:13]2[C:18](=[CH:19][C:20]([O:21][CH3:22])=[C:11]([O:10][CH3:9])[CH:12]=2)[CH:17]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:30])[CH3:2]

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 214870076,7-dimethoxy-1-phenyl-3,4-dihydro-2(1H)-isoquinolinecarbonyl chloride

Product 1

HCID 21486957HCID 21486957, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10 parts by volume of 2-diethylaminoethylamine is added 3.0 parts of 6,7-dimethoxy-1-phenyl-3,4-dihydro-2(1H)-isoquinolinecarbonyl chloride. An exothermic reaction ensues. The mixture is heated over a steam bath for approximately 30 minutes. (Alternatively, the mixture is maintained at room temperature overnight.) The reaction mixture is then poured into water and extracted with ethyl ether. The ether layer is dried over anhydrous calcium sulfate and evaporated to dryness. The solid thus obtained is crystallized from a mixture of ethyl ether and n-hexane to afford N-(2-diethylaminoethyl)-6,7-dimethoxy-1-phenyl-3,4-dihydro-2(1H)-isoquinolinecarboxamide, melting at about 97°-98°C.

Workup

  1. customAn exothermic reaction
  2. temperatureThe mixture is heated over a steam bath for approximately 30 minutes
  3. extractionextracted with ethyl ether
  4. dry with materialThe ether layer is dried over anhydrous calcium sulfate
  5. customevaporated to dryness
  6. customThe solid thus obtained
  7. customis crystallized from a mixture of ethyl ether and n-hexane

Sources & evidence

ORD record
ord-78f928b92249456fb86c9502fac5b461
Source dataset
uspto-grants-1977_01
Patent number
US04001244

Reaction notes

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