1-(3-Chlorophenyl)piperazine → Hydrochloric Acid

HRID 2291734Notes

Reaction equation

HRID 2291734 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:15][CH2:16][O:17][C:18]([C:20]1[C:32]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]=2[CH:23]=[CH:22][CH:21]=1)=[O:19].C(N(CC)CC)C.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:52].Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][O:17][C:18]([C:20]3[C:32]4[CH2:31][C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:24]=4[CH:23]=[CH:22][CH:21]=3)=[O:19])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[ClH:52]

Participants

7

Reactant 4

HCID 13551-(3-Chlorophenyl)piperazineHCID 8471TriethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 53739950HCID 53739950, compound

Product 2

HCID 313Hydrochloric AcidYield 31%HCID 54107750HCID 54107750, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-bromoethanol (3.3 g, 0.026 mol) in 50 mL of methylene chloride, fluorene-1-carboxylic acid chloride (6 g, 0.026 mol) and triethylamine (5 g, 0.05 mol) were added. The reaction mixture was stirred at room temperature overnight. The methylene chloride was washed with water, dried over anhydrous Na2SO4 and removed under reduced pressure to afford 7 g of the intermediate fluorene-1-carboxylic acid bromoethyl ester. The title compound was prepared by stirring 4-(3-chlorophenyl)piperazine (2.6 g, 0.011 mol), fluorene-1-carboxylic acid bromoethyl ester (3.5 g, 0.011 mol) and triethylamine (2.5 g, 0.025 mol) in 50 mL of CH2Cl2 for 24 hours. The methylene chloride was washed with water, dried (anhydrous Na2SO4) and removed under reduced pressure. The remaining residue was subjected to preparative HPLC over silica gel using ethylacetate as the eluent and the desired product (TLC Rf =0.68 in 30% methanol/ethylacetate system) was separated and converted to the dihydrochloride salt with ethanolic HCl (1.8 g, 31% yield), mp. 215°-217° C.

Workup

  1. washThe methylene chloride was washed with water
  2. dry with materialdried (anhydrous Na2SO4)
  3. customremoved under reduced pressure
  4. customthe desired product (TLC Rf =0.68 in 30% methanol/ethylacetate system) was separated

Sources & evidence

ORD record
ord-e483ba830704446f87078c4801b22c8b
Source dataset
uspto-grants-1989_01
Patent number
US04797489

Reaction notes

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