Water → Ethyl 4-(piperidin-1-yl)benzoate

HRID 427283

Reaction equation

HRID 427283 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O>C(#N)C>[N:13]1([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Product 1

HCID 13813852Ethyl 4-(piperidin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Reaction of ethyl 4-fluorobenzoate with piperidine (3 equivalents) in acetonitrile was carried out at reflux for 4 days. Dilution of the cooled reaction mixture with several volumes of water provided a precipitate, which was filtered to provide ethyl 4-(piperidin-1-yl)benzoate. Reduction of the ester with lithium aluminum hydride (2 equivalents) in tetrahydrofuran gave the corresponding alcohol (Examples 71, 72).

Workup

  1. temperatureat reflux for 4 days
  2. customprovided a precipitate, which
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-c8b15264a4eb4c2e9a59dd9bdeae15d9
Source dataset
uspto-grants-2001_11
Patent number
US06313100B1

Linked notes

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