Water → HCID 67169245, compound

HRID 2170865Notes

Reaction equation

HRID 2170865 reaction equation
Cl.[Cl:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[C:24]([C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1)=[O:25].O>ClCCl>[Cl:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([C:24]([C:26]3[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=3)=[O:25])[CH2:12][CH2:13]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 177497914-(4-Chlorophenoxy)piperidine hydrochloride

Product 1

HCID 67169245HCID 67169245, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(4-chlorophenoxy)piperidine hydrochloride (250 mg, 1.01 mmol), and triethylamine (0.56 mL, 4.03 mmol) in dichloromethane (10 mL) was added methyl 4-(chlorocarbonyl)benzoate (220 mg, 1.11 mmol) at room temperature. After stirring at room temperature for 2 hours, the mixture was poured into water (30 mL). This was extracted with dichloromethane (30 mL) and washed with water (30 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (eluting with n-hexane/ethyl acetate=3/1) to give 329 mg (87% yield) of the title compound as a white solid.

Workup

  1. extractionThis was extracted with dichloromethane (30 mL)
  2. washwashed with water (30 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography (eluting with n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-55f1c3f2675c43d997a545016995451a
Source dataset
uspto-grants-2015_06
Patent number
US09051296B2

Reaction notes

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