Piperidin-4-ol → Hpr 611

HRID 66310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 66310
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Na].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[S:17][C:16](=[O:18])[N:15]([CH2:19][C:20](OC)=[O:21])[C:14]=2[CH:24]=1>C[O-].[Na+].CO>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:20]([CH2:19][N:15]2[C:14]3[CH:24]=[C:10]([Cl:9])[CH:11]=[CH:12][C:13]=3[S:17][C:16]2=[O:18])=[O:21])[CH2:4][CH2:3]1

Komponenten

6

Edukt 3

HCID 79341Piperidin-4-olHCID 5360545SodiumHCID 13040939Methyl 2-oxo-5-chloro-3-benzothiazolineacetate

Produkt 1

HCID 3082453Hpr 611Ausbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 10942334Sodium MethoxideLösungsmittel

Versuchsvorschrift

4-Hydroxypiperidine (47.2 g) was added at room temperature to and dissolved in a methanolic sodium methoxide solution prepared from sodium metal (2.2 g) in dry methanol (100 ml). To the resultant solution was added methyl 5-chloro-2-oxo-3-benzothiazolineacetate (100 g), and the mixture was heated for 3 hours under reflux with stirring. The reaction mixture was left to cool, poured into ice water (500 ml) and stirred for 30 minutes. The precipitates were collected, washed with water and then dried to give 3-(4-hydroxypiperidino)carbonylmethyl-5-chloro-2-benzothiazolinone (102.5 g), which was recrystallized from 90% aqueous methanol to give colorless crystals, m.p. 180.1° C.

Aufarbeitung

  1. temperaturethe mixture was heated for 3 hours
  2. temperatureunder reflux
  3. waitThe reaction mixture was left
  4. temperatureto cool
  5. stirringstirred for 30 minutes
  6. customThe precipitates were collected
  7. washwashed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-96b26f98857542468026d27821d2f913
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04131681

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