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Methanol → 3-(4-Methoxybenzylamino)-4-hydroxy-alpha-(tert-butylaminomethyl)benzyl alcohol hydrochloride

HRID 616212
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 616212
[ClH:1].[NH2:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[OH:17])[CH:6]([OH:13])[CH2:7][NH:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1.CO>O=[Pt]=O.O>[ClH:1].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:2][C:3]2[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=2[OH:17])[CH:6]([OH:13])[CH2:7][NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:22][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 887MethanolHCID 312444-MethoxybenzaldehydeHCID 13416921HCID 13416921, Verbindung

Produkt 1

HCID 1629243-(4-Methoxybenzylamino)-4-hydroxy-alpha-(tert-butylaminomethyl)benzyl alcohol hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysator
HCID 962
Water
Lösungsmittel

Versuchsvorschrift

A mixture of 3-amino-4-hydroxy-α-(tert.butylaminomethyl)-benzylalcohol hydrochloride (6.53 g, 0.025 mole), p-methoxybenzaldehyde (3.4 g, 0.025 mole), PtO2 (180 mg), and methanol (125 ml) was placed in a hydrogenation apparatus and hydrogenated at normal pressure (20 - 30 cm H2O superatmospheric) for one hour and 50 minutes. During this period of time, the calculated amount of hydrogen was absorbed, and the hydrogenation was interrupted by supplying argon. The platinum catalyst was filtered off with continued supply of argon, but in spite of this, the filtrate quickly became dark due to oxidation. The filtrate was immediately evaporated in vacuum at 40° - 50° C. The residue which was a light brown foam (9.53 g), was recrystallized twice by precipitation from ethanol/ether (1:1). The yield of the analytical pure 3-(4-methoxybenzylamino)-4-hydroxy-α-(tert.butylaminomethyl)benzylalcohol hydrochloride was 5.2 g (55%), m.p. 196.6° - 197.8° C.

Aufarbeitung

  1. waitDuring this period of time
  2. customthe calculated amount of hydrogen was absorbed
  3. filtrationThe platinum catalyst was filtered off with continued supply of argon
  4. customThe filtrate was immediately evaporated in vacuum at 40° - 50° C
  5. customwas recrystallized twice by precipitation from ethanol/ether (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-90df2bbbc53547ccb0f9b0244b9ec91a
Quelldatensatz
uspto-grants-1978_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04072760

Notizen zur Reaktion

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