Hydrochloric Acid → HCID 70348252, compound

HRID 477482Notes

Reaction equation

HRID 477482 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][OH:16])[C:6]=1[CH:7]=O.C([O-])(=O)C.[NH4+].C([BH3-])#[N:23].[Na+].[ClH:26]>CO>[ClH:26].[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][OH:16])[C:6]=1[CH2:7][NH2:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 19835683HCID 19835683, compound

Product 1

HCID 70348252HCID 70348252, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.08 g of 2,6-bis(2-hydroxyethoxy)benzaldehyde dissolved in 100 ml of anhydrous methanol are treated with 15.6 g of ammonium acetate and 12 g of sodium cyanoborohydride, then stirred under nitrogen blanket at 25°-30° C. for 48 hours, then adjusted to pH=1 with concentrated hydrochloric acid and evaporated at reduced pressure. The solid residue is treated with 30 ml of water and extracted with 20 ml of ethyl acetate, said volume being divided previously into two portions. The water phase, after elimination of the small amount of ethyl acetate dissolved, such removal being carried out under reduced pressure, is adjusted to pH=11 with a 25% solution of potassium hydroxide and then extracted with tetrahydrofuran. The extracts are dried with anhydrous potassium carbonate, then evaporated under reduced pressure, dissolved with 30 ml of a 1/1 mixture of tetrahydrofuran/ethyl ether, and afterwards saturated with gaseous hydrogen chloride and filtered. The solid, after washing with anhydrous ethyl ether, drying under reduced pressure and crystallization from a mixture of ethanol/acetonitrile, gives 2,6-bis(hydroxyethoxy)benzylamine hydrochloride with a yield of 92%; melting point is 166°-168° C. I.R. (KBr), 3325 cm-1 (OH), 2605 cm-1 (NH3+), 1262 cm-1 (aromatic C--O), 779 cm-1 (phenyl).

Workup

  1. customevaporated at reduced pressure
  2. additionThe solid residue is treated with 30 ml of water
  3. extractionextracted with 20 ml of ethyl acetate
  4. dissolutionThe water phase, after elimination of the small amount of ethyl acetate dissolved
  5. customsuch removal
  6. extractionextracted with tetrahydrofuran
  7. dry with materialThe extracts are dried with anhydrous potassium carbonate
  8. customevaporated under reduced pressure
  9. dissolutiondissolved with 30 ml of a 1/1 mixture of tetrahydrofuran/ethyl ether
  10. filtrationafterwards saturated with gaseous hydrogen chloride and filtered
  11. washThe solid, after washing with anhydrous ethyl ether
  12. dry with materialdrying under reduced pressure and crystallization from a mixture of ethanol/acetonitrile

Sources & evidence

ORD record
ord-60866f1f6ca94f52ac06ff038f46759e
Source dataset
uspto-grants-1989_12
Patent number
US04888283

Reaction notes

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