Diethylethanolamine → 2-Diethylaminoethyl 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionate hydrochloride

HRID 2419903Notes

Reaction equation

HRID 2419903 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][OH:6])[CH3:2].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:35]=[CH:34][C:19]([CH2:20][O:21][C:22]([C:30]([F:33])([F:32])[F:31])([C:26]([F:29])([F:28])[F:27])[C:23](Cl)=[O:24])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1>N1C=CC=CC=1>[ClH:9].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([CH2:20][O:21][C:22]([C:26]([F:27])([F:28])[F:29])([C:30]([F:31])([F:32])[F:33])[C:23]([O:6][CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])=[O:24])=[CH:34][CH:35]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7497DiethylethanolamineHCID 203144652-[4-(4-Chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionyl chloride

Product 1

HCID 203144772-Diethylaminoethyl 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionate hydrochlorideYield 112.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-diethylaminoethanol (814 mg.) and pyridine (10 ml.) is added at 0° C. to 2-[4-(4-chlorophenyl)-benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionyl chloride (3.07 g.). The mixture is stirred at room temperature until the acid chloride dissolves, and the solution is stored at 0° C. for 2 days. The mixture is filtered and the filtrate evaporated. The residue is triturated with ether and combined with the solid previously filtered off. The combined solids are crystallised from dioxane-ether to give 2-diethylaminoethyl 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionate hydrochloride (2.2 g.), m.p. 139°-140° C. (decomposition).

Workup

  1. dissolutiondissolves
  2. filtrationThe mixture is filtered
  3. customthe filtrate evaporated
  4. customThe residue is triturated with ether
  5. filtrationpreviously filtered off
  6. customThe combined solids are crystallised from dioxane-ether

Sources & evidence

ORD record
ord-66426c7d31754f978d77cbae7f1892f9
Source dataset
uspto-grants-1978_08
Patent number
US04107329

Reaction notes

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