Piperidine → HCID 9928115, compound

HRID 1729183Notes

Reaction equation

HRID 1729183 reaction equation
Cl[CH2:2][C:3]([C:5]1[N:6]([CH3:19])[CH:7]=[C:8]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:9]=1)=[O:4].[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]([C:8]2[CH:9]=[C:5]([C:3](=[O:4])[CH2:2][N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[N:6]([CH3:19])[CH:7]=2)=[O:18])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 104941282-Chloro-1-[4-(4-chlorobenzoyl )-1-methyl-1H-pyrrol-2-yl]-ethanone

Product 1

HCID 9928115HCID 9928115, compoundYield 81.4%

Procedure

A solution of 4 g (0.013 mole) of 2-chloro-1-[4-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-2-yl]-ethanone (11) and 4.08 mL (0.039 mole) of piperidine in 60 mL 2-PrOH was heated under reflux for 1 h. The solvent was evaporated in vacuo and the residue was taken up in diethyl ether/THF, washed with water, brine, and dried (MgSO4). Evaporation of the solvent gave a tan solid which was recrystallized from 2-PrOH to give 3.65 g of product: mp 129°-130° C.; mass spectrum (Cl--CH4) m/z=345 (M+1); NMR 300 MHz (CDCl3) d 7.8 (m, 2H); 7.6 (s, 1H); 7.45 (d, 2H); 7.35 (s, 1H); 4.0 (s, 3H); 3.6 (s, 2H); 2.5 (br s, 4H); 1.6 (m, 4H); 1.4 (m, 2H). Anal Calcd for C19H21Cl2N2O2 : C, 66.18; H, 6.14; N, 8.12. Found: C, 66.25; H, 6.16; N, 8.08.

Workup

  1. temperatureunder reflux for 1 h
  2. customThe solvent was evaporated in vacuo
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent
  6. customgave a tan solid which
  7. customwas recrystallized from 2-PrOH

Sources & evidence

ORD record
ord-b82a1081c36a47dd817f822390ff8807
Source dataset
uspto-grants-1994_07
Patent number
US05332736

Reaction notes

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