Water → HCID 86585670, compound

HRID 2187469Notes

Reaction equation

HRID 2187469 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:17](C(C)C)CC)(C)C.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>ClCCl>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23]([NH2:17])=[O:30])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 317384-BenzylpiperidineHCID 81531Diisopropylethylamine

Product 1

HCID 86585670HCID 86585670, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-benzylpiperidine (0.263 g, 1.5 mM) and diisopropylethyl-amine (0.53 mL, 3.0 mM) in 10 mL dichloromethane at room temperature was added benzoyl chloride (0.281 g, 2.0 mM) and the reaction mixture was stirred at room temperature for 20 h. The reaction mixture was poured into water and extracted with ethyl acetate (2×25 mL). The combined organic extract was washed with 1 N HCl, water and brine. The extract was dried over Na2SO4 and evaporated. The residue was chromatographed on a column of silica gel with ethyl acetate-hexane (10 to 50%, gradient). Evaporation of the desired fractions gave 0.402 g (96%) of the title compound as an oil. 1H NMR (CDCl3): δ 7.10-7.40 (m, 10H), 4.60-4.70 (m, 1H), 3.70-3.80 (m, 1H), 2.80-2.90 (m, 1H), 2.70-2.80 (m, 1H), 2.60 (d, 2H), 1.70-1.80 (m, 1H), 1.50-1.70 (m, 2H), 1.20-1.40 (m, 2H). MS (ESI) m/e 279 (M+).

Workup

  1. extractionextracted with ethyl acetate (2×25 mL)
  2. extractionThe combined organic extract
  3. washwas washed with 1 N HCl, water and brine
  4. dry with materialThe extract was dried over Na2SO4
  5. customevaporated
  6. customThe residue was chromatographed on a column of silica gel with ethyl acetate-hexane (10 to 50%, gradient)
  7. customEvaporation of the desired fractions

Sources & evidence

ORD record
ord-3a394f54937047f6ae9b9989d6261b6e
Source dataset
uspto-grants-2002_06
Patent number
US06410540B1

Reaction notes

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