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

HRID 973302Notes

Reaction equation

HRID 973302 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 dioxan-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 dioxan-ether

Sources & evidence

ORD record
ord-bb8d44ad1d8846f4a4c253f386cc1f4b
Source dataset
uspto-grants-1977_10
Patent number
US04055595

Reaction notes

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