Hydrochloric Acid → 1,5-Diamino-1-(2-benzyloxyethyl)-3-aza-pentane hydrochloride

HRID 1733797Notes

Reaction equation

HRID 1733797 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]([C:32](=O)[NH:33][CH2:34][CH2:35][NH:36]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[NH:12]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:57]>CO>[ClH:57].[NH2:12][CH:11]([CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:32][NH:33][CH2:34][CH2:35][NH2:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 194385562-(2-Benzyloxyethyl)-3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptane

Product 1

HCID 194385261,5-Diamino-1-(2-benzyloxyethyl)-3-aza-pentane hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2-Benzyloxyethyl)-3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptane is reacted in a manner analogous to the reaction of step (c) of Example 9 up to the point where the purified product is taken up in methanol and conc. hydrochloric acid is added. From this point the method described by M. Bessodes et al., Tetr. Lett., (1986) 579 to remove the triphenylmethyl protecting groups is employed: the product is taken up in a mixture of formic acid and diethylether and refluxed for several hours. After evaporation to dryness the product is dissolved in water, the pH is adjusted to 10 and the product is extracted with chloroform. The organic phase is evaporated and the product is taken up in dry ethanol. Dry hydrogen chloride gas is bubbled through the stirred solution cooled with an ice/water bath, and 1,5-diamino-1-(2-benzyloxy-ethyl)-3-azapentane hydrochloride is collected by filtration.

Workup

  1. custom, (1986) 579 to remove the triphenylmethyl protecting groups
  2. additionthe product is taken up in a mixture of formic acid and diethylether
  3. temperaturerefluxed for several hours
  4. customAfter evaporation to dryness the product
  5. dissolutionis dissolved in water
  6. extractionthe product is extracted with chloroform
  7. customThe organic phase is evaporated
  8. customDry hydrogen chloride gas is bubbled through the stirred solution
  9. temperaturecooled with an ice/water bath
  10. filtration1,5-diamino-1-(2-benzyloxy-ethyl)-3-azapentane hydrochloride is collected by filtration

Sources & evidence

ORD record
ord-1188fbbacbdf4d3b86819107b8ff5f47
Source dataset
uspto-grants-1996_07
Patent number
US05531978

Reaction notes

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