Water → 2-Methyl-5-(trifluoromethyl)phenyl 4-{4-[(cyclohexyloxy)carbonyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

HRID 1888099Notes

Reaction equation

HRID 1888099 reaction equation
[C:1](Cl)(=[O:14])[O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[CH3:13].[Cl-].[CH:17]1([O:23][C:24]([C:26]2[N:27]=[C:28]([CH:31]3[CH2:36][CH2:35][NH2+:34][CH2:33][CH2:32]3)[S:29][CH:30]=2)=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(N(C(C)C)CC)(C)C.O>ClCCl>[CH:17]1([O:23][C:24]([C:26]2[N:27]=[C:28]([CH:31]3[CH2:32][CH2:33][N:34]([C:1]([O:2][C:3]4[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=4[CH3:13])=[O:14])[CH2:35][CH2:36]3)[S:29][CH:30]=2)=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 669115194-{4-[(Cyclohexyloxy)carbonyl]-1,3-thiazol-2-yl}piperidinium chlorideHCID 866602322-Methyl-5-(trifluoromethyl)phenyl chlorocarbonate

Product 1

HCID 866602312-Methyl-5-(trifluoromethyl)phenyl 4-{4-[(cyclohexyloxy)carbonyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, 2-methyl-5-(trifluoromethyl)phenyl chlorocarbonate (239 mg) is added to a solution of 4-{4-[(cyclohexyloxy)carbonyl]-1,3-thiazol-2-yl}piperidinium chloride (VII-1, 324 mg) and diisopropylethylamine (323 mg) in dichloromethane (8 ml). The mixture is stirred at room temperature overnight, and water is then added. The aqueous phase is separated off and extracted with ethyl acetate, and the combined organic phases are then dried with sodium sulphate. The solid is filtered off and the solvent is removed by distillation. The residue is purified chromatographically. This gives 2-methyl-5-(trifluoromethyl)phenyl 4-{4-[(cyclohexyloxy)carbonyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (193 mg, 39%).

Workup

  1. customThe aqueous phase is separated off
  2. extractionextracted with ethyl acetate
  3. dry with materialthe combined organic phases are then dried with sodium sulphate
  4. filtrationThe solid is filtered off
  5. customthe solvent is removed by distillation
  6. customThe residue is purified chromatographically

Sources & evidence

ORD record
ord-69fc3fec76814f3190d3425460196ab9
Source dataset
uspto-grants-2013_08
Patent number
US08501781B2

Reaction notes

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