Triethylamine → HCID 20225284, compound

HRID 1249206Notes

Reaction equation

HRID 1249206 reaction equation
[CH3:1][O:2][CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)[CH2:4][NH2:5].[C:13]([CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:21][CH:20]=1)([O:15][CH3:16])=[O:14].C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O>[C:13]([CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][NH:5][CH2:4][CH:3]([O:2][CH3:1])[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=2)=[CH:23][CH:24]=1)([O:15][CH3:16])=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 20225197HCID 20225197, compoundHCID 20225281HCID 20225281, compound

Product 1

HCID 20225284HCID 20225284, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 2-methoxy-2-(3-chlorophenyl)ethanamine (1.81 g), 2-(4-carbomethoxymethoxyphenyl)-1-(p-toluenesulphonyloxy)ethane (4.0 g) and triethylamine (4 ml) in dimethyl sulphoxide (50 ml) was heated at 55° C. After 24 h the solution was poured into saturated sodium carbonate solution and the aqueous layer extracted with dichloromethane. The organic extract was separated, dried and evaporated. Chromatography over silica gel (eluting with 2% methanol-dichloromethane) gave N-[2-(4-carbomethoxymethoxyphenyl)ethyl]-2-methoxy-2-(3-chlorophenyl)ethanamine which was converted into the title compound, mp 167°-169° C. (ethyl acetate-hexane) by an analogous procedure to that described in Example 4.

Workup

  1. extractionthe aqueous layer extracted with dichloromethane
  2. extractionThe organic extract
  3. customwas separated
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-905a23805edb43e9bbf4b1fd0f52fcfd
Source dataset
uspto-grants-1986_12
Patent number
US04629737

Reaction notes

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