Pyridine → HCID 66885559, compound

HRID 1364295Notes

Reaction equation

HRID 1364295 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].N1C=CC=CC=1.[S:14]1[CH:18]=[CH:17][C:16]2[C:19]([N:23]3[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][O:32][C:33]4[CH:42]=[C:41]5[C:36]([CH2:37][CH2:38][CH2:39][NH:40]5)=[CH:35][CH:34]=4)[CH2:25][CH2:24]3)=[CH:20][CH:21]=[CH:22][C:15]1=2.C(Cl)[Cl:44]>>[ClH:44].[C:1]([N:40]1[C:41]2[C:36](=[CH:35][CH:34]=[C:33]([O:32][CH2:31][CH2:30][CH2:29][N:26]3[CH2:25][CH2:24][N:23]([C:19]4[C:16]5[CH:17]=[CH:18][S:14][C:15]=5[CH:22]=[CH:21][CH:20]=4)[CH2:28][CH2:27]3)[CH:42]=2)[CH2:37][CH2:38][CH2:39]1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 66885568HCID 66885568, compound

Product 1

HCID 66885559HCID 66885559, compoundYield 52%

Procedure

Acetic anhydride (0.34 ml, 3.6 mmol) and pyridine (0.34 ml, 4.3 mmol) were added to a solution of 7-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1,2,3,4-tetrahydroquinoline (0.49 g, 1.2 mmol) in methylene chloride (10 ml) with cooling in an ice-bath, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and water and ethyl acetate were added to the residue to separate the organic phase from the water phase. The organic phase was washed with water, saturated sodium hydrogencarbonate aqueous solution and brine in this order, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=1:1), and concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (10 ml), and 1N—HCl—ethanol solution was added thereto. Then, crystals precipitated were filtered out and dried to obtain 1-acetyl-7-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1,2,3,4-tetrahydroquinoline hydrochloride (0.27 q, yield: 52%) as white powder.

Workup

  1. temperaturewith cooling in an ice-bath
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and water and ethyl acetate
  3. additionwere added to the residue
  4. customto separate the organic phase from the water phase
  5. washThe organic phase was washed with water, saturated sodium hydrogencarbonate aqueous solution and brine in this order
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=1:1)
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe resulting residue was dissolved in ethyl acetate (10 ml)
  10. addition1N—HCl—ethanol solution was added
  11. customThen, crystals precipitated
  12. filtrationwere filtered out
  13. customdried

Sources & evidence

ORD record
ord-26d8b77096574a43924cacf4a15754aa
Source dataset
uspto-grants-2011_02
Patent number
US07888362B2

Reaction notes

Loading…