Triethylamine → Tetrafluoro-m-phenylenediamine dihydrochloride

HRID 2290481Notes

Reaction equation

HRID 2290481 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH2:8]Cl)=[CH:4][CH:3]=1.[C:12]1([NH2:23])[C:17]([F:18])=[C:16]([F:19])[C:15]([F:20])=[C:14]([NH2:21])[C:13]=1[F:22].[ClH:24].Cl.[N:26]1([CH2:32][CH:33]([C:35]2[CH:43]=[CH:42][C:38]([C:39]([O-:41])=[O:40])=[CH:37][CH:36]=2)[CH3:34])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[CH2:44](N(CC)CC)[CH3:45]>C(Cl)Cl>[C:12]1([NH2:23])[C:17]([F:18])=[C:16]([F:19])[C:15]([F:20])=[C:14]([NH2:21])[C:13]=1[F:22].[ClH:1].[ClH:24].[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH2:8][N:29]2[CH2:30][CH2:31][N:26]([CH2:32][CH:33]([C:35]3[CH:43]=[CH:42][C:38]([C:39]([O:41][CH2:44][CH3:45])=[O:40])=[CH:37][CH:36]=3)[CH3:34])[CH2:27][CH2:28]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 20232701HCID 20232701, compoundHCID 53728250p-Chlorocinnamyl chloride

Product 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 53673856HCID 53673856, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By the reaction of 4-chlorocinnamyl chloride with the dihydrochloride of 4-[1-(piperazin-1-yl)-prop-2-yl]-benzoate in methylene chloride in the presence of triethylamine (analogously to Example 25), there is obtained a yield of 81% of theory of the dihydrochloride of ethyl 4-{1-[1-(4-chlorocinnamyl)-piperazin-4-yl]-prop-2-yl}-benzoate; m.p. 249°-250° C. (recrystallised from ethanol).

Sources & evidence

ORD record
ord-3498e60470764de69c91d8d677669b74
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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