Benzoyl chloride → 1-(4-Benzoyloxybenzyl)-1,2,3,6-tetrahydropyridine

HRID 236554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 236554
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][C:11]1[CH:23]=[CH:22][C:14]([CH2:15][N:16]2[CH2:21][CH:20]=[CH:19][CH2:18][CH2:17]2)=[CH:13][CH:12]=1.[OH-].[Na+].CC1C=CC(COC(NNC(C2C=NC=CN=2)=O)=O)=CC=1>CCOCC>[C:1]([O:10][C:11]1[CH:23]=[CH:22][C:14]([CH2:15][N:16]2[CH2:17][CH:18]=[CH:19][CH2:20][CH2:21]2)=[CH:13][CH:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamateHCID 202160941-(4-Hydroxybenzyl)-1,2,3,6-tetrahydropyridine

Produkt 1

HCID 202161341-(4-Benzoyloxybenzyl)-1,2,3,6-tetrahydropyridineAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Benzoyl chloride (3.0 g.) was added to a vigorously stirred mixture of 1-(4-hydroxybenzyl)-1,2,3,6-tetrahydropyridine (4.0 g.) in N-sodium hydroxide solution (22 ml.) and ether (30 ml.). The mixture was stirred for 2 hours after the addition and then 3N-sodium hydroxide solution added to pH10. The subsequent mixture was extracted into ethyl acetate (2×30 ml.) and the combined extracts were dried (MgSO4) and evaporated. The residue was dissolved in acetone (50 ml.) and the solution was treated with concentrated hydrochloric acid to pH2. The solid which precipitated was collected by filtration and recrystallised from isopropanol to give 1-(4-benzoyloxybenzyl)-1,2,3,6-tetrahydropyridine (1.8 g.), m.p. 220°-227° C.

Aufarbeitung

  1. additionafter the addition
  2. extractionThe subsequent mixture was extracted into ethyl acetate (2×30 ml.)
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. customevaporated
  5. dissolutionThe residue was dissolved in acetone (50 ml.)
  6. additionthe solution was treated with concentrated hydrochloric acid to pH2
  7. customThe solid which precipitated
  8. filtrationwas collected by filtration
  9. customrecrystallised from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-9a3309f6520b43f5944e73a1eb230cdf
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04645771

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