Potassium Iodide → HCID 70027421, compound

HRID 1368066Notes

Reaction equation

HRID 1368066 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[NH:12][CH:11]=[C:10]([C:13](=[O:21])[CH2:14][N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:9]=2)=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:25][N:26]([CH2:28][CH2:29][CH2:30]Cl)[CH3:27].C([O-])([O-])=O.[K+].[K+].[I-].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]([CH:28]([N:26]([CH3:27])[CH3:25])[CH2:29][CH3:30])[CH:11]=[C:10]([C:13](=[O:21])[CH2:14][N:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)[CH:9]=2)=[O:7])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 18519868HCID 18519868, compound

Product 1

HCID 70027421HCID 70027421, compoundYield 29.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2 g (0.006 mole) of 1-[5-(4-chlorobenzoyl)-1H-pyrrol-3-yl]-2-(1-piperidinyl)ethanone, 1.4 g (0.0078 mole) of dimethylaminopropyl chloride hydrochloride, 5.2 g (0.042 mole) of K2CO3, and 1 g (0.006 mole) of potassium iodide in 40 mL of DMF was stirred overnight then heated to 70° C. for 5 h. After cooling the reaction mixture was poured into water, and extracted with Et2O. The organics were washed with water, brine and dried (K2CO3). The solvent was evaporated in vacuo and treated with ethereal HCl in 2-PrOH to give 0.73 g (29%) of Compound 14. mp 138-141° C. CIMS m/z416 (MH+). 1H NMR (300 MHz, DMSO-d6) δ 8.35 (Ar, 1H); 7.8 (Ar, 2H); 7.7 (Ar, 2H); 7.2 (Ar, 1H); 4.8 (m, 2H); 4.6 (t, 2H); 3.4 (m, 3H); 3.15-2.9 (m, 4H); 2.75 (d, 6H); 2.2 (m, 2H); 1.9-1.65 (m, 4H); 1.4 (m, 1H). Anal calc'd for: C23H30CIN3O2. 2HCl.1.3H2O: C, 54.00; H, 6.80; N, 8.21. Found: C, 53.69; H, 6.89; N, 7.93 KF 4.04.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted with Et2O
  3. washThe organics were washed with water, brine
  4. dry with materialdried (K2CO3)
  5. customThe solvent was evaporated in vacuo
  6. additiontreated with ethereal HCl in 2-PrOH

Sources & evidence

ORD record
ord-cb40fc7d89394bc9b0c8c716cf7399bd
Source dataset
uspto-grants-2003_06
Patent number
US06573267B2

Reaction notes

Loading…