3-Hydroxybenzaldehyde → 1-(3-Hydroxybenzyl)piperidine

HRID 35591

Reaktionsgleichung

Reaktionsgleichung von HRID 35591
[BH4-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.Cl>C(O)C.O>[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Komponenten

7

Edukt 4

HCID 1013-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 8082PiperidineHCID 4311764Sodium borohydride

Produkt 1

HCID 8269741-(3-Hydroxybenzyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium borohydride (1.52 g) was added to a stirred solution of 3-hydroxybenzaldehyde (4.9 g) and piperidine (6.8 g) in ethanol (25 ml) cooled in an ice-water bath. The mixture was stirred at ambient temperature for 16 hours and then poured into water (250 ml) and the resulting mixture acidified with 2N hydrochloric acid. The acidified mixture was extracted with ethyl acetate and the aqueous phase was made alkaline by the addition of aqueous ammonia solution (S.G. 0.880) to yield N-3-hydroxybenzylpiperidine (m.p. 135°-139° C.) as a colourless solid.

Aufarbeitung

  1. temperaturecooled in an ice-water bath
  2. extractionThe acidified mixture was extracted with ethyl acetate
  3. additionby the addition of aqueous ammonia solution (S.G. 0.880)

Quellen und Nachweise

ORD-Eintrag
ord-89f7153ba59246a183e586c34cf69726
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767769

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