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Acetic Acid → 4-Amino-3-[(1-benzyl-piperidin-4-yl-amino)-methyl]phenol

HRID 1353601
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1353601
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=[O:27])C>[Zn]>[NH2:22][C:17]1[CH:18]=[CH:19][C:20]([OH:27])=[CH:21][C:16]=1[CH2:15][NH:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 176Acetic AcidHCID 48487621-benzyl-N-[(2-nitrophenyl)methyl]piperidin-4-amine

Produkt 1

HCID 588643124-Amino-3-[(1-benzyl-piperidin-4-yl-amino)-methyl]phenolAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23994ZincKatalysator

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(1-Benzyl-piperidin-4-yl)-(2-nitro-benzyl)-amine (0.25 g, 0.7 mmol) and zinc dust (0.2 g, excess) were combined in 75% aqueous acetic acid (8 mL) and stirred at 60° C. for 2 h. After cooling to room temperature, the solvents were removed in vacuo and the resultant crude mixture dissolved in water (10 mL), followed by addition of ammonium hydroxide until pH 3 was attained. The solution was extracted with methylene chloride (3×). The organic layers were pooled together, washed with water (2×), brine (2×), dried over sodium sulfate, filtered, and concentrated to afford 0.18 g (79%) of the desired product.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe solvents were removed in vacuo
  3. dissolutionthe resultant crude mixture dissolved in water (10 mL)
  4. additionfollowed by addition of ammonium hydroxide until pH 3
  5. extractionThe solution was extracted with methylene chloride (3×)
  6. washwashed with water (2×), brine (2×)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-36d2593855fb48988e1af1f51847c936
Quelldatensatz
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07220862B2

Notizen zur Reaktion

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