Water → 1-(3-Benzoylpropyl)-4-benzamidopiperidine

HRID 849991Notes

Reaction equation

HRID 849991 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[C:13]([NH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].O>C(Cl)(Cl)Cl>[C:5]([CH2:4][CH2:3][CH2:2][N:25]1[CH2:26][CH2:27][CH:22]([NH:21][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:23][CH2:24]1)(=[O:6])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 118120N-4-PiperidylbenzamideHCID 2535334-Chlorobutyrophenone

Product 1

HCID 100892541-(3-Benzoylpropyl)-4-benzamidopiperidineYield 9.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4-chlorobutyrophenone (447 mg, 2.45 mmol), 4-benzamidopiperidine (500 mg, 2.45 mmol) and K2CO3 (338 mg, 2.45 mmol) was heated up in boiling water bath for 1 hour. The reaction mixture was portioned between water and CHCl3. The organic layer was separated and dried over Na2SO4. After filtration and removal of solvent, the residue was purified by chromatography (SiO2, MeOH:CHCl3, 5:95). Recrystallization from AcOEt/hexane gave a white powder (78 mg, 8.2%). mp 143-144° C.; 1H NMR (CD3OD, 400 MHz) δ 1.65 (dq, J1 =3.16 Hz, J2 =11.9 Hz, 2H), 1.90-2.00 (m, 4H), 2.18 (t, J=11.9 Hz, 2H), 2.48 (m, 2H), 3.00-3.10 (m, 4H), 3.88 (m, 1H), 7.40-8.00 (m, 10H); Mass spectrum (M+1)+ at m/z 351.

Workup

  1. temperaturewas heated up
  2. customfor 1 hour
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and removal of solvent
  6. customthe residue was purified by chromatography (SiO2, MeOH:CHCl3, 5:95)
  7. customRecrystallization from AcOEt/hexane

Sources & evidence

ORD record
ord-6d77d0bd98764607b21cd3acb6cb1e81
Source dataset
uspto-grants-2000_01
Patent number
US06015819

Reaction notes

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