Benzoyl chloride → 4-Piperidineethanol, 1-benzoyl-

HRID 1655964Notes

Reaction equation

HRID 1655964 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][OH:18])[CH2:12][CH2:11]1.C(N(CC)CC)C>ClCCl>[C:1]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][OH:18])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 739534-Piperidineethanol

Product 1

HCID 104214984-Piperidineethanol, 1-benzoyl-Yield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (13.3 mL, 0.115 mole) was added dropwise over 0.5 hour to a 0° C. solution of 4-piperidineethanol (14.8 g, 0.115 mole) and dry triethylamine (18 mL, 0.13 mole) in dichloromethane with mechanical stirring. After 16 hours at room temperature, the mixture was quenched with 1.0 M aqueous NaOH (150 mL), then extracted with ethyl acetate (1 L). The organic phase was extracted further with H2O (125 mL), then brine (125 mL), dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by chromatography on silica gel, eluting with chloroform to 6% methanol in chloroform, followed by concentration in vacuo and drying at 100° C. under high vacuum for 1.5 hour to yield a viscous oil (25.1 g, 94%). IR (neat): 3409 cm-1 (s,br), 1613(s). HRMS: Calculated for C14H19NO2 : 233.1416; found: 233.1410.

Workup

  1. customthe mixture was quenched with 1.0 M aqueous NaOH (150 mL)
  2. extractionextracted with ethyl acetate (1 L)
  3. extractionThe organic phase was extracted further with H2O (125 mL)
  4. dry with materialbrine (125 mL), dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by chromatography on silica gel
  8. washeluting with chloroform to 6% methanol in chloroform
  9. concentrationfollowed by concentration in vacuo
  10. customdrying at 100° C. under high vacuum for 1.5 hour

Sources & evidence

ORD record
ord-fd0f641e2c544a96a59ab2a0aef8439b
Source dataset
uspto-grants-1993_10
Patent number
US05252586

Reaction notes

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