Triethylamine → 9-[1-(2,2,2-Trichloroethoxycarbonyl)-4-piperidylidene]xanthene

HRID 36610

Reaction equation

HRID 36610 reaction equation
C[N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:21]3[CH:20]=[CH:19][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.C(N(CC)CC)C.[Cl:29][C:30]([Cl:37])([Cl:36])[CH2:31][O:32][C:33](Cl)=[O:34].[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:29][C:30]([Cl:37])([Cl:36])[CH2:31][O:32][C:33]([N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[O:15][C:16]3[C:21]2=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:4][CH2:3]1)=[O:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 100391731-Methyl-4-xanthen-9-ylidene-piperidine

Product 1

HCID 152894789-[1-(2,2,2-Trichloroethoxycarbonyl)-4-piperidylidene]xanthene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 430 mg (1.55 mmol) of 1-methyl-4-(9H-xanthene-9-ylidene)piperidine [Tetrahedron Letters, 29, 5701 (1988)] and 649 μL (4.65 mmol) of triethylamine in 20 mL of dry toluene at 85° C. under an atmosphere of argon was added over 10 min 1.06 mL (7.7 mmol) of 2,2,2-trichloroethyloxycarbonyl chloride. After 30 min the mixture was cooled to room temperature, poured into a solution of 25% aqueous sodium hydroxide, and was extracted with ethyl acetate (3×). The combined organic portions were dried over sodium sulfate, filtered, and concentrated with vacuo to afford the title compound as a crude oil.

Workup

  1. extractionwas extracted with ethyl acetate (3×)
  2. dry with materialThe combined organic portions were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated with vacuo

Sources & evidence

ORD record
ord-56a04910b677402a8876a4b78d2c3b06
Source dataset
uspto-grants-1995_05
Patent number
US05416087

Linked notes

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