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Triethylamine → (2R,5R)-1-((4-chlorophenoxy)methyl)carbonyl-2-methyl4-(4-fluorobenzyl)-5-((hydroxy)methyl)piperazine

HRID 1263549
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1263549
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[CH2:12][C@H:11]([CH3:13])[NH:10][CH2:9][C@@H:8]2[CH2:14][OH:15])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:25][C:26]1[CH:36]=[CH:35][C:29]([O:30][CH2:31][C:32](Cl)=[O:33])=[CH:28][CH:27]=1>C(Cl)Cl>[Cl:25][C:26]1[CH:36]=[CH:35][C:29]([O:30][CH2:31][C:32]([N:10]2[CH2:9][C@H:8]([CH2:14][OH:15])[N:7]([CH2:6][C:5]3[CH:16]=[CH:17][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:12][C@H:11]2[CH3:13])=[O:33])=[CH:28][CH:27]=1
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 77771p-Chlorophenoxyacetyl chlorideHCID 57226061(2R,5S)-1-(4-fluorobenzyl)-2-(hydroxy)methyl-5-methylpiperazine

Produkt 1

HCID 11441144(2R,5R)-1-((4-chlorophenoxy)methyl)carbonyl-2-methyl4-(4-fluorobenzyl)-5-((hydroxy)methyl)piperazineAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

To a solution of (2R,5S)-1-(4-fluorobenzyl)-2-(hydroxy)methyl-5-methylpiperazine (1.6 g, 6.7 mmol) in CH2Cl2 (30 mL) was added triethylamine (excess) and 4-chlorophenoxyacetyl chloride (1.5 g, 7.4 mmol, dropwise in 10 mL solution of CH2Cl2). The resultant mixture was stirred at ambient temperature. After 20 minutes, analysis by analytical TLC showed complete consumption of starting material had occurred. The mixture was concentrated of volatiles in vacuo and the residue taken up in CH2Cl2. This was washed with saturated aqueous NaHCO3 solution, then water, then brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel afforded 2.16 g (79% yield) of (2R,5R)-1-((4-chlorophenoxy)methyl)carbonyl-2-methyl-4-(4-fluorobenzyl)-5-((hydroxy)methyl)piperazine, as a solid yellow foam: NMR (DMSO-d6) 7.7 (br s, 2), 7.3 (m, 4), 6.9 (d, 2), 5.0-4.2 (m, 5), 4.0-3.2 (m, 7), 1.2 (m, 3) ppm; MS (LSIMS) 406.

Aufarbeitung

  1. customconsumption of starting material
  2. concentrationThe mixture was concentrated of volatiles in vacuo
  3. washThis was washed with saturated aqueous NaHCO3 solution
  4. dry with materialwater, then brine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f11cbeabd9514098945d94773a17fbf5
Quelldatensatz
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06541476B1

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