1,1-Dichloroethane → HCID 18403870, compound

HRID 1017680Notes

Reaction equation

HRID 1017680 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:50]C(Cl)C>>[ClH:50].[ClH:50].[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][N:33]2[CH2:34][CH2:35][N:30]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=3)[CH2:31][CH2:32]2)=[CH:11][C:10]=1[O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 944591-(2-Pyridyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 18403741HCID 18403741, compound

Product 1

HCID 18403870HCID 18403870, compoundYield 42.1%

Procedure

To a solution of 4-benzyloxy-3-(ethoxycarbonylmethoxy)benzaldehyde (0.2 g) in dichloroethane (4 ml) was added (pyridin-2-yl)piperazine (0.12 ml) and sodiumtriacetoxy borohydride (0.25 g), with stirring. The reaction mixture was stirred at ambient temperature for 1.5 hrs, poured into ice/saturated sodium bicarbonate solution and extracted with ethyl acetate. The extracts were washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was dissolved in dichloromethane and flash chromatographed (silica gel), eluting with dichloromethane, 1% and 2% methanol/dichloromethane. The appropriate fractions were collected and concentrated. The residue was dissolved in ether and ethereal hydrochloric acid was added. The suspension was filtered and the filter cake dried for 2 hrs at ambient temperature. Recrystallization from ethanol provided 0.143 g (42.1%) of product, mp 151-191° C.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 1.5 hrs
  2. additionpoured into ice/saturated sodium bicarbonate solution
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water, saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. dissolutionThe residue was dissolved in dichloromethane
  9. customflash chromatographed (silica gel)
  10. washeluting with dichloromethane, 1% and 2% methanol/dichloromethane
  11. customThe appropriate fractions were collected
  12. concentrationconcentrated
  13. dissolutionThe residue was dissolved in ether
  14. additionethereal hydrochloric acid was added
  15. filtrationThe suspension was filtered
  16. customthe filter cake dried for 2 hrs at ambient temperature
  17. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-24a81b5616ff4b9b807afda8b276b6ba
Source dataset
uspto-grants-2002_11
Patent number
US06479495B1

Reaction notes

Loading…