Potassium Carbonate → 1-(3-Benzoylpropyl)-4-benzamidopiperidine

HRID 1720953Notes

Reaction equation

HRID 1720953 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+]>>[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

4

Reactant 3

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

Product 1

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

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 partitioned 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, 400MHz) 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 reaction mixture was partitioned between water and CHCl3
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and removal of solvent
  7. customthe residue was purified by chromatography (SiO2, MeOH:CHCl3, 5:95)
  8. customRecrystallization from AcOEt/hexane

Sources & evidence

ORD record
ord-63daa09d702a41dcb6d85c73e5f9d1b6
Source dataset
uspto-grants-1996_04
Patent number
US05508306

Reaction notes

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