Ethyl 1-benzylpiperidine-4-carboxylate → 1-Benzylpiperidine-4-carbaldehyde

HRID 22283

Reaktionsgleichung

Reaktionsgleichung von HRID 22283
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](OCC)=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 90423Ethyl 1-benzylpiperidine-4-carboxylateHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 895841-Benzylpiperidine-4-carbaldehydeAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of ethyl 1-benzylpiperidine-4-carboxylate (9.2 g, 0.037 mol) in 400 ml of toluene was added 1.5M diisobutylaluminum hydride in toluene (28 ml, 0. 042 mol) at -78° C. The mixture was stirred at -78° C. for 1 hr and quenched with 150 ml of MeOH and the dry ice bath was removed. After stirring for 2 hr at r.t., the mixture was filtered through diatomaceous earth (Celite (trademark)) and washed with methanol. The filtrate was concentrated to dryness to give 6.91 g (92%) of 1-benzylpiperidine-4-carboxaldehyde which can be used directly or purified by vacuum distillation, bp 93°-97° C./1 mmHg. HNMR (CDCl3)δ 1.6-1.8 (m, 2H), 1.8-1.9 (m, 2H), 2.05-2.17 (m, 2H), 2.17-2.3 (m, 1H), 2.75-2.9 (m, 2H), 3.5 (s, 2H), 7.2-7.4 (m, 5H), 9.6 (s, 1H) ppm.

Aufarbeitung

  1. customquenched with 150 ml of MeOH
  2. customthe dry ice bath was removed
  3. stirringAfter stirring for 2 hr at r.t.
  4. filtrationthe mixture was filtered through diatomaceous earth (Celite (trademark))
  5. washwashed with methanol
  6. concentrationThe filtrate was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f3939a0025d4433eadbaa330b94b97c1
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428043

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