Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]- → HCID 22630903, compound

HRID 2416459Notes

Reaction equation

HRID 2416459 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([N:10]2[CH:14]=[CH:13][CH:12]=[N:11]2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[Br-].[O:16]1CCO[CH:17]1[CH2:21][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOCCN(CCOCCOC)CCOCCOC>ClCCl.C([O-])([O-])=O.[K+].[K+]>[F:1][C:2]1[CH:9]=[C:8]([N:10]2[CH:14]=[CH:13][CH:12]=[N:11]2)[CH:7]=[CH:6][C:3]=1/[CH:4]=[CH:21]/[CH:17]=[O:16]

Participants

6

Reactant 3

HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 2724194(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromideHCID 226310262-Fluoro-4-(1H-pyrazol-1-yl)benzaldehyde

Product 1

HCID 22630903HCID 22630903, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 11430Potassium CarbonateSolvent

Procedure

A mixture of 2-fluoro-4-(1H-pyrazol-1-yl)benzaldehyde (1.06 g, 5.57 mmol, prepared as described in Reference Example 8), (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide (3.60 g, 8.39 mmol), and TDA-1 (1.80 mL, 5.63 mmol) in dichloromethane (30 mL) and sat. aq. K2CO3 (30 mL) was heated to reflux for 20 h. The layers were separated and the aqueous layer was extracted with dichloromethane (2×15 mL). The combined organic layers were washed with water (30 mL) and brine (30 mL), dried (Na2SO4), and concentrated. THF (15 mL) and 10% HCl (15 mL) were added and the mixture was stirred for 1 h at rt. The mixture was cooled to 0° C., the precipitated solids were removed by filtration, washed with water and dried in vacuo. Recrystallization from IPA provided 0.84 g (70%) of the title compound as tan needles. MS 217 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×15 mL)
  5. washThe combined organic layers were washed with water (30 mL) and brine (30 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. additionTHF (15 mL) and 10% HCl (15 mL) were added
  9. temperatureThe mixture was cooled to 0° C.
  10. customthe precipitated solids were removed by filtration
  11. washwashed with water
  12. customdried in vacuo
  13. customRecrystallization from IPA

Sources & evidence

ORD record
ord-c3a44c412b264ab28037b65d438ad63e
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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