Hydrochloric Acid → HCID 53827300, compound

HRID 865792Notes

Reaction equation

HRID 865792 reaction equation
Cl.[C:2](#[N:4])[CH3:3].CO.C(N(CC)CC)C.C1C=[C:18]2[C:20]([C:22](O)([OH:25])[C:23](=[O:24])C2=CC=1)=[O:21]>C1COCC1>[NH2:4][CH2:2][CH2:3][CH2:18][CH:20]([CH:22]([CH2:23][OH:24])[OH:25])[OH:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10236NinhydrinHCID 87252791HCID 87252791, compound

Product 1

HCID 53827300HCID 53827300, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Aminopropyl solketal (2.43 g 12.8 mmole) was dissolved in THF (30 ml) and aqueous hydrochloric acid (1M, 30 ml) was added. After 1 hour at room temperature TLC (acetonitrile/methanol/triethlyamine 80/18/2) indicated that all starting material Rf 0.33 had been hydrolyzed to the diol Rf ca.0.0 (detection by ninhydrin spray). THF was evaporated in vacuo and the aqueous residue was applied to a Dowex 50 ion exchange column (100 ml, H form). The resin was washed with water to remove all Cl ion and the desired amine was eluted with aqueous ammonia. The ammonia solution was evaporated to remove all volatile material and the aqueous residue used for subsequent reactions without further purification.

Workup

  1. customTHF was evaporated in vacuo
  2. washThe resin was washed with water
  3. customto remove all Cl ion
  4. washthe desired amine was eluted with aqueous ammonia
  5. customThe ammonia solution was evaporated
  6. customto remove all volatile material
  7. customthe aqueous residue used for subsequent reactions without further purification

Sources & evidence

ORD record
ord-e817049d280e44a6adf5bb438b9bfbbd
Source dataset
uspto-grants-1996_10
Patent number
US05567811

Reaction notes

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