Hydrochloric Acid → 1-[3-(4-Chlorobenzoyl)propyl]-4-benzamidopiperidine

HRID 2085436Notes

Reaction equation

HRID 2085436 reaction equation
[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O-:19])([O-])=O.[K+].[K+].[ClH:22]>CC(C)=O>[Cl:22][C:2]1[CH:7]=[CH:6][C:5]([C:16]([CH2:11][CH2:10][CH2:15][N:13]2[CH2:14][CH2:15][CH:10]([NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:11][CH2:12]2)=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 118120N-4-Piperidylbenzamide

Product 1

HCID 102713911-[3-(4-Chlorobenzoyl)propyl]-4-benzamidopiperidine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-(4-chlorobenzol)propyl bromide (640 mg, 2.45 mmol), 4-benzamidopiperidine (500 mg, 2.45 mmol) and K2CO3 (1.01 g, 7.34 mmol) in 50 ml of acetone was heated at reflux temperature for 48 h. The cooled reaction mixture was filtered to remove the solids, concentrated in vacuo, giving a yellow solid, which was purified by chromatography (MeOH/CHCl3, 5/95). The product (320 mg 33.9%) was isolated as a white powder: 1H NMR δ 1.46 (dq, J1=1.0 Hz, J2=8.4 Hz, 2H), 1.90-2.10 (m, 4H), 2.16 (m, 2H), 2.43 (t, J=6.9 Hz, 2H), 2.80-2.90 (m, 2H), 2.97 (t, J=6.9 Hz, 2H), 3.97 (m, 1H), 5.92 (d, J=7.8 Hz, 1H, N—H), 7.40-8.00 (m, 9H). The product was converted to the HCl salt and recrystallized from MeOH/Et2O, m.p. 243-244° C.; Anal. Calcd for C22H25ClN2O2+HCl+H2O: C, 60.15; H, 6.37; N, 6.37; Found: C, 60.18; H, 6.34; N, 6.29.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 48 h
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customto remove the solids
  6. concentrationconcentrated in vacuo
  7. customgiving a yellow solid, which
  8. customwas purified by chromatography (MeOH/CHCl3, 5/95)
  9. customThe product (320 mg 33.9%) was isolated as a white powder
  10. customrecrystallized from MeOH/Et2O, m.p. 243-244° C.

Sources & evidence

ORD record
ord-add88e483c7e4c77864094a396395f6c
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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