Nitrogen → HCID 86738314, compound

HRID 2059186Notes

Reaction equation

HRID 2059186 reaction equation
[Cl-].[C:2]1([CH:8]([C:14]([O-:16])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][NH2:29])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26].N#N.[Cl-].C([NH+](CC)CC)C>O1CCCC1.C(N(CC)CC)C>[C:2]1([CH:8]([C:14]([O-:16])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][NH-:29])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]

Participants

7

Reactant 4

HCID 947NitrogenHCID 8421HomoveratrylamineHCID 12698378Triethylazanium chlorideHCID 20546023HCID 20546023, compound

Product 1

HCID 86738314HCID 86738314, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

Two hundred ninety-five grams (1.3 mol) of monoethyl phenylmalonate chloride in 500 ml of absolute tetrahydrofuran were added dropwise, at room temperature, to a cooled mixture of 236 gm (1.3 mol) of 2-(3',4'-dimethoxyphenyl)-ethylamine, 171 gm of triethylamine, and 500 ml of absolute tetrahydrofuran, under stirring and in a protective N2 atmosphere. After the reaction ended, the precipitated triethylammonium chloride was suction filtered, the filtrate was concentrated, and the solid residue was distributed between water and methylene chloride. The organic phase was dried over Na2SO4. After the solvent evaporated, the product was recrystallized from ethyl acetate.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customAfter the solvent evaporated
  5. customthe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-bf37caff152440c48cdd3fc7c9de596b
Source dataset
uspto-grants-1982_03
Patent number
US04322418

Reaction notes

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