Triethylamine → HCID 13674889, compound

HRID 1649999Notes

Reaction equation

HRID 1649999 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[NH:15][CH2:16][CH:17]([N:19]([CH3:21])[CH3:20])[CH3:18].C(N(CC)CC)C>ClCCCl>[CH3:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH3:7])[C:9]=1[N:15]([CH2:16][CH:17]([N:19]([CH3:21])[CH3:20])[CH3:18])[C:2]([O:4][CH2:5][CH3:6])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 134365N~1~-(2,6-Dimethylphenyl)-N~2~,N~2~-dimethylpropane-1,2-diamine

Product 1

HCID 13674889HCID 13674889, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

0.78 ml (0.88 g, 8 mmoles) of ethyl chloroformate are added to a mixture of 1.0 g (4.85 mmoles) of 1-(2,6-dimethylphenyl-amino)-2-dimethylamino-propane, prepared as described in Example 8, 0.60 ml (0.51 g, 5 mmoles) of triethylamine and 20 ml of 1,2-dichloroethane, and the reaction mixture is boiled for 6 hours. The mixture is washed thrice with 10 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The oily residue is subjected to column chromatography on 20 g of silica gel, applying ethyl acetate as eluant. 0.91 g (67.4%) of 1-[N-(2,6-dimethylphenyl)-N-ethoxycarbonyl-amino]-2-dimethylamino-propane are obtained as a light yellow, oily substance. The hydrochloride of this base melts at 165°-167° C.

Workup

  1. customprepared
  2. washThe mixture is washed thrice with 10 ml of water
  3. dry with materialeach, dried over anhydrous magnesium sulfate
  4. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-c757ec65283a462ea8ebbdd2c64bfc11
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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