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3-Chloro-4-methylaniline → HCID 59376130, Verbindung

HRID 1400200
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1400200
C[Al](C)C.[Cl:5][C:6]1[CH:7]=[C:8]([NH2:13])[CH:9]=[CH:10][C:11]=1[CH3:12].C([O:16][C:17]([C@H:19]1[CH2:24][CH2:23][CH2:22][N:21]([C:25](=[O:33])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[C@H:20]1[C:34]1[CH:39]=[CH:38][C:37]([NH:40][CH:41]2[CH2:45][CH2:44][CH2:43][CH2:42]2)=[CH:36][CH:35]=1)=O)C>ClC(Cl)C.C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]([NH:13][C:17]([C@H:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25](=[O:33])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[C@H:20]2[C:34]2[CH:39]=[CH:38][C:37]([NH:40][CH:41]3[CH2:45][CH2:44][CH2:43][CH2:42]3)=[CH:36][CH:35]=2)=[O:16])[CH:9]=[CH:10][C:11]=1[CH3:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 72553-Chloro-4-methylanilineHCID 16682925TrimethylaluminumHCID 59376115HCID 59376115, Verbindung

Produkt 1

HCID 59376130HCID 59376130, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel
HCID 6365
1,1-Dichloroethane
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Me3Al (290 μL, 0.57 mmol, 2M in toluene) was added to a solution of the 3-Chloro-4-methylphenylamine (65 mg, 0.46 mmol) in dry dichloroethane (1 mL) at ambient temperature. Stirred for 20 minutes, then (2R,3S)-2-(4-Cyclopentylaminophenyl)-1-(2-methylbenzoyl)piperidine-3-carboxylic acid ethyl ester (100 mg, 0.23 mmol) dissolved in dry dichloroethane (1 mL) was added to it. The reaction mixture was then heated to 85° C. for 3 h, cooled to r.t, diluted with CH2Cl2 (20 mL), washed with saturated aqueous NaHCO3 solution. The aqueous layer was extracted with CH2Cl2 (20 mL) and the combined organic layer was dried (MgSO4) and concentrated. The residue was purified by reverse phase preparative HPLC (20-95% gradient of CH3CN—H2O with 0.1% TFA as additive), the product containing fractions were pooled together and concentrated. The residue was diluted with CH2Cl2 (30 mL), washed with saturated aqueous NaHCO3 solution. The CH2Cl2 layer was dried (MgSO4) and concentrated to get the pure (2R,3S)-2-(4-Cyclopentylaminophenyl)-1-(2-methylbenzoyl)piperidine-3-carboxylic acid (3-chloro-4-methylphenyl)amide in 50% yield.

Aufarbeitung

  1. additionwas added to it
  2. temperaturecooled
  3. washwashed with saturated aqueous NaHCO3 solution
  4. extractionThe aqueous layer was extracted with CH2Cl2 (20 mL)
  5. dry with materialthe combined organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by reverse phase preparative HPLC (20-95% gradient of CH3CN—H2O with 0.1% TFA as additive)
  8. additionthe product containing fractions
  9. concentrationconcentrated
  10. additionThe residue was diluted with CH2Cl2 (30 mL)
  11. washwashed with saturated aqueous NaHCO3 solution
  12. dry with materialThe CH2Cl2 layer was dried (MgSO4)
  13. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-24e02cacdeef4a5daa15531a8207845e
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08906938B2

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