Propionic Acid → 1-Methyl-4-[2-(trifluoromethyl)-9H-xanthen-9-ylidene]piperidine

HRID 2083753Notes

Reaction equation

HRID 2083753 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2(O)[C:21]3[CH:20]=[C:19]([C:22]([F:25])([F:24])[F:23])[CH:18]=[CH:17][C:16]=3[O:15][C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:4][CH2:3]1.S(C1C=CC=CC=1C(OC(=O)C1C=CC=CC=1S(O)(=O)=O)=O)(O)(=O)=O.C(O)(=O)CC.[OH-].[Na+]>O>[CH3:1][N:2]1[CH2:3][CH2:4][C:5](=[C:8]2[C:21]3[CH:20]=[C:19]([C:22]([F:25])([F:23])[F:24])[CH:18]=[CH:17][C:16]=3[O:15][C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 1032Propionic AcidHCID 14798Sodium HydroxideHCID 13795534Sulphobenzoic anhydrideHCID 203575299-(1-Methylpiperidin-4-YL)-2-(trifluoromethyl)-9H-xanthen-9-OL

Product 1

HCID 203575141-Methyl-4-[2-(trifluoromethyl)-9H-xanthen-9-ylidene]piperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Dehydration of the xanthene-9-ol (88.2 g., 0.24 m.) is accomplished by refluxing with 88.1 g. (0.48 m.) of sulfobenzoic anhydride and 1.2 1. of propionic acid for two hours. The reaction mixture is heated in vacuo at 100° C. and the residual syrup is dissolved in water and made strongly basic with 40% sodium hydroxide solution. Extraction with ether gives 1-methyl-4-(2-trifluoromethyl-9-xanthenylidene)-piperidine, m.p. 82°-83° C.

Workup

  1. temperatureby refluxing with 88.1 g
  2. extractionExtraction with ether

Sources & evidence

ORD record
ord-ede74644681e4b3aac23b61d8e71411c
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

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