Hydrochloric Acid → HCID 59296091, compound

HRID 2233388Notes

Reaction equation

HRID 2233388 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:23]=[CH:22][C:7]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[C:6]([C:24]([O:26]C)=[O:25])[CH:5]=1.Cl>O1CCCC1>[C:18]([O:17][C:15]([N:12]1[CH2:11][CH2:10][CH:9]([O:8][C:7]2[CH:22]=[CH:23][C:4]([Cl:3])=[CH:5][C:6]=2[C:24]([OH:26])=[O:25])[CH2:14][CH2:13]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59295936HCID 59295936, compound

Product 1

HCID 59296091HCID 59296091, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution of 2N sodium hydroxide (20 ml) was added to a solution of tert-butyl 4-[4-chloro-2-(methoxycarbonyl) phenoxy]piperidine-1-carboxylate (8.1 g, 22.0 mmol) in tetrahydrofuran (70 ml) at 45° C. The mixture was stirred vigorously for 3 h then adjusted to pH 2 with 2N hydrochloric acid. The product was extracted with ethyl acetate and the organic layer washed repeatedly with water until the washings were pH 6. The organic layer was dried over magnesium sulfate and evaporated. The residue was azeotroped with toluene to give the title compound as a colourless solid (7.5 g).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washthe organic layer washed repeatedly with water until the washings
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-b436ce8b352041d68bc2e7cc44f2c2ed
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

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