Water → 2-[1-(3-Methoxybenzoyl)piperidin-4-yl]ethanol

HRID 54550

Reaction equation

HRID 54550 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.C(N(CC)CC)C.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](Cl)=[O:23].O>C(Cl)Cl>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([N:7]1[CH2:8][CH2:9][CH:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]1)=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 739534-PiperidineethanolHCID 74374m-Anisoyl chloride

Product 1

HCID 199591682-[1-(3-Methoxybenzoyl)piperidin-4-yl]ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-(2-hydroxyethyl)piperidine (5.0 g) and triethylamine (5.39 ml) in methylene chloride (50 ml) was added dropwise a solution of 3-methoxybenzoyl chloride (5.44 ml) in methylene chloride (15 ml) at 0° C. After stirring at ambient temperature for 1 hour, the mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine, and dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica eluting with chloroform and the fractions containing the object product were collected and evaporated to give 2-[1-(3-methoxybenzoyl)piperidin-4-yl]ethanol (9.6 g) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica eluting with chloroform
  6. additionthe fractions containing the object product
  7. customwere collected
  8. customevaporated

Sources & evidence

ORD record
ord-acddf5e7728249bc8a7f2cb00ab35d79
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Linked notes

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