Potassium Carbonate → HCID 15053402, compound

HRID 1032168Notes

Reaction equation

HRID 1032168 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]1.C(=O)([O-])[O-].[K+].[K+].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2([OH:38])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[CH:28][CH:27]=1>O1CCCC1.O>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2([OH:38])[CH2:33][CH2:34][N:35]([C:11]([N:9]3[CH2:10][CH:7]([O:6][C:5]4[CH:14]=[CH:15][CH:16]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=4)[CH2:8]3)=[O:12])[CH2:36][CH2:37]2)=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 197996061-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine

Product 1

HCID 15053402HCID 15053402, compoundYield 113.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 2.8 g (0.01 mole) of 3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride and 1.4 g (0.01 mole) of potassium carbonate in 25 ml of tetrahydrofuran was treated with 2 g (0.01 mole) of 4-(4-chlorophenyl)-4-hydroxypiperidine added in small portions. After stirring for 30 min, a few pieces of ice were added and stirring continued for 16 hr. The reaction mixture was diluted with 200 ml of water and the oil which separated was extracted into methylene chloride (2×50 ml). The combined extracts were dried over magnesium sulfate and concentrated in vacuo to give a water-like oil (5.16 g). A crystalline solid was obtained by cooling to -78° C. and recrystallization was accomplished by dissolving the residue in 5 ml of acetone and 75 ml of isopropyl ether and reducing the volume under nitrogen to 40 ml. Upon cooling, filtration yielded 3.6 g (79.1%) of fine white crystals, m.p. 127°-128.5° C.

Workup

  1. additionadded in small portions
  2. additiona few pieces of ice were added
  3. stirringstirring
  4. waitcontinued for 16 hr
  5. customthe oil which separated
  6. extractionwas extracted into methylene chloride (2×50 ml)
  7. dry with materialThe combined extracts were dried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fbbb9ca166464c3a84a1ae02cf594644
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

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