Triethylamine → Hydrochloric Acid

HRID 2291733Notes

Reaction equation

HRID 2291733 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]([C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:7].[CH2:18]([N:20](CC)[CH2:21][CH3:22])[CH3:19].[C:25]1(N)[C:30](F)=[C:29](F)[C:28](F)=[C:27]([NH2:34])[C:26]=1F.[ClH:37].Cl>C(Cl)Cl>[Cl:37][C:29]1[CH:28]=[C:27]([N:34]2[CH2:22][CH2:21][N:20]([CH2:2][CH2:3][CH2:4][O:5][C:6]([C:8]34[CH2:17][CH:12]5[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]5)[CH2:9]3)[CH2:15]4)=[O:7])[CH2:18][CH2:19]2)[CH:26]=[CH:25][CH:30]=1.[ClH:37]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 14373539HCID 14373539, compound

Product 2

HCID 313Hydrochloric AcidYield 20%HCID 10621874HCID 10621874, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-bromopropanol (5.56 g, 0.04 mol) in 50 mL of methylene chloride, adamantane-1-carboxylic acid chloride (5.6 g, 0.02 mol) and triethylamine (4 g, 0.04 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 12 g of the intermediate adamantane-1-carboxylic acid bromopropyl ester. The title compound was prepared by stirring 4-(3-chlorophenyl)-1-piperazine (2.7 g, 0.011 mol), adamantane-1-carboxylic acid bromopropyl 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 =0.6 in 30% methanol/ethylacetate) was separated and converted to the dihydrochloride salt with ethanolic HCl (1 g, 20% yield), mp. 220°-222° 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 =0.6 in 30% methanol/ethylacetate) was separated

Sources & evidence

ORD record
ord-532b73a612854f3c9a5269d1470ffa7f
Source dataset
uspto-grants-1989_01
Patent number
US04797489

Reaction notes

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