Water → HCID 20269145, compound

HRID 485832Notes

Reaction equation

HRID 485832 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][NH:5][C:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([OH:9])[CH2:7][CH3:8].N1C=CC=CC=1.Cl[C:27]([O:29][CH2:30][CH3:31])=[O:28].O>CCOCC>[CH2:30]([O:29][C:27]([NH:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][NH:5][C:6]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([OH:9])[CH2:7][CH3:8])=[O:28])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10928Ethyl chloroformateHCID 20250781HCID 20250781, compound

Product 1

HCID 20269145HCID 20269145, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.6 g (0.01 mole) of N-2-amino-benzyl-1-phenyl-2-methyl-amino-1-ethanol are dissolved in 30 ml of ether. To the solution 0.79 g (0.01 mole) of anhydrous pyridine are added, whereupon 1.3 g (0.012 mole) of ethyl chloroformate are added under vigorous stirring and cooling and the reaction is carried out at 15° C. The reaction mixture which contains a white precipitate is stirred at room temperature for 330 minutes, poured into 30 ml of icecold water, the aqueous phase is extracted three times with 100 ml of ether each, the united ether extracts are dried over anhydrous sodium sulfate and evaporated in vacuo. Thus 2.8 g of N-[2-ethoxycarbonylamino-benzyl]-1-phenyl-2-methyl-amino-1-ethanol are obtained in the form of a yellowish-white oil which can be subjected to further reaction without purification.

Workup

  1. temperaturecooling
  2. customis carried out at 15° C
  3. stirringis stirred at room temperature for 330 minutes
  4. extractionthe aqueous phase is extracted three times with 100 ml of ether each, the united ether extracts
  5. dry with materialare dried over anhydrous sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-4fcf4e5e7b0d4c1a87743591061d3369
Source dataset
uspto-grants-1985_08
Patent number
US04537895

Reaction notes

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