Potassium Carbonate → Tert-butyl 4-(3-(4-(2,2,2-trifluoroethoxy)phenoxy)benzylidene)piperidine-1-carboxylate

HRID 1666526Notes

Reaction equation

HRID 1666526 reaction equation
[OH:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:24]=[CH:25][CH:26]=2)[CH:10]=[C:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:36][C:37]([F:40])([F:39])[F:38]>CN(C)C=O>[F:38][C:37]([F:40])([F:39])[CH2:36][O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:24]=[CH:25][CH:26]=2)[CH:10]=[C:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:13][CH2:12]2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 66876036Tert-butyl 4-(3-(4-hydroxyphenoxy)benzylidene)piperidine-1-carboxylate

Product 1

HCID 66876113Tert-butyl 4-(3-(4-(2,2,2-trifluoroethoxy)phenoxy)benzylidene)piperidine-1-carboxylateYield 27.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 4-(3-(4-hydroxyphenoxy)benzylidene)piperidine-1-carboxylate (150 mg, 0.393 mmol) in dimethylformamide (5 mL) was treated with potassium carbonate (218 mg, 1.572 mmol), 18-crown ether (210 mg, 0.786 mmol) and 2-iodo-1,1,1 trifluoroethane (105 mg, 0.491 mmol). The mixture was stirred overnight at a temperature below 50° C. The reaction mixture was washed with water and organic part extracted with ether (2×50 mL). The organic fractions were dried over sodium sulfate and evaporated. The crude material was purified by column chromatography (10-20% ethyl acetate/hexanes) to give the title compound (50 mg, 27%). 1H-NMR (500 MHz, CDCl3): δ ppm 7.26 (m, 1H), 7.00 (d, J=6 Hz, 2H), 6.94 (m, 3H), 6.80 (m, 2H), 6.29 (s, 1H), 4.36 (m, 2H), 3.49 (s, 2H), 3.38 (s, 2H), 2.42 (s, 2H), 2.30 (s, 2H), 1.47 (s, 9H).

Workup

  1. washThe reaction mixture was washed with water and organic part
  2. extractionextracted with ether (2×50 mL)
  3. dry with materialThe organic fractions were dried over sodium sulfate
  4. customevaporated
  5. customThe crude material was purified by column chromatography (10-20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b866644efbd44d818f0557d49245a664
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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