1-(2-Hydroxyethyl)piperazine → HCID 14373548, compound

HRID 2291736Notes

Reaction equation

HRID 2291736 reaction equation
FC1C=CC=CC=1C#N.OCCN1CCNCC1.[OH:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]#[N:35])[CH2:24][CH2:23]1.C(N(C(C)C)CC)(C)C.[C:45]12([C:55](Cl)=[O:56])[CH2:54][CH:49]3[CH2:50][CH:51]([CH2:53][CH:47]([CH2:48]3)[CH2:46]1)[CH2:52]2>CN(C)C=O.C(Cl)Cl>[C:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[N:25]1[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][O:19][C:55]([C:45]23[CH2:54][CH:49]4[CH2:48][CH:47]([CH2:53][CH:51]([CH2:50]4)[CH2:52]2)[CH2:46]3)=[O:56])[CH2:23][CH2:24]1)#[N:35]

Participants

8

Reactant 5

HCID 76771-(2-Hydroxyethyl)piperazineHCID 678552-FluorobenzonitrileHCID 81531DiisopropylethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 17514071HCID 17514071, compound

Product 1

HCID 14373548HCID 14373548, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

2-Fluorobenzonitrile (6.0 g, 50 mmoles) and 1-(2-hydroxyethyl)-piperazine (6.5 g, 50 mmoles) were combined in 500 mL of dimethylformamide and heated at 80° C. under N2 for 24 hours. After cooling, the solvent was removed in vacuum and the crude 1-(2-hydroxyethyl)-4-(2-cyanophenyl)piperazine thus produced was used without purification. 2.3 Grams (10 mmole) of the crude 1-(2-hydroxyethyl)-4-(2-cyanophenyl)piperazine was dissolved in 100 mL of CH2Cl2 and 1.3 g (10 mmole) of diisopropyl ethylamine was added, followed by addition of 2.0 g (10 mmole) of 1-adamantanecarbonyl chloride. The mixture was stirred at room temperature for 3 hours, washed with saturated NaHCO3 solution, saturated brine, dried over Na2SO4, filtered and concentrated in vacuum. The residue was column chromatographed on 100 g of silica gel with CHCl3 and the product thus obtained was crystallized from isopropanol with the addition of 4N isopropanolic HCl to give 1.1 g of title compound as the monohydrochloride salt, mp. 230°-231° C.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed in vacuum
  3. customthe crude 1-(2-hydroxyethyl)-4-(2-cyanophenyl)piperazine thus produced
  4. customwas used without purification
  5. washwashed with saturated NaHCO3 solution, saturated brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum
  9. customchromatographed on 100 g of silica gel with CHCl3
  10. customthe product thus obtained
  11. customwas crystallized from isopropanol with the addition of 4N isopropanolic HCl

Sources & evidence

ORD record
ord-5a49b28e9f4943cfb23d0093c6c25be1
Source dataset
uspto-grants-1989_01
Patent number
US04797489

Reaction notes

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