Benzene → 2-Aminopropyl-5-(naphthalen-1-yl)-1,3-dioxane hydrochloride

HRID 1613330Notes

Reaction equation

HRID 1613330 reaction equation
[ClH:1].C(OC(OCC)[CH2:6][CH2:7][CH2:8][NH2:9])C.[C:13]1([CH:23]([CH2:26][OH:27])[CH2:24][OH:25])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.[CH:28]1C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[ClH:1].[NH2:9][CH:8]([CH3:28])[CH2:7][CH:6]1[O:25][CH2:24][CH:23]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)[CH2:26][O:27]1

Participants

6

Reactant 4

HCID 241Benzene2×HCID 313Hydrochloric AcidHCID 806724,4-DiethoxybutylamineHCID 146425962-(Naphthalen-1-yl)propane-1,3-diol

Product 1

HCID 197757382-Aminopropyl-5-(naphthalen-1-yl)-1,3-dioxane hydrochloride

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

Sufficient ethereal hydrogen chloride is added to 4 g (25 mmol) of 4,4-diethoxybutylamine in 500 ml of benzene to precipitate all the hydrochloride. 4 g (20 mmol) of 2-(naphthalen-1-yl)propane-1,3-diol in 200 ml of benzene and 100 mg of paratoluenesulphonic acid are then added, and the mixture is evaporated to dryness in a bath at 100° C. A further 700 ml of benzene are added, the mixture is evaporated under the same conditions, and the residue is then placed in vacuo at 100 C for 4 h. It is recrystallised in diethyl ether, dried at 60° C., recrystallised twice in ethanol, treating it with vegetable charcoal during the first recrystallisation, washed with diethyl ether and dried at 80° C. 3.2 g (10.4 mmol) of product are obtained.

Workup

  1. customto precipitate all the hydrochloride
  2. customthe mixture is evaporated to dryness in a bath at 100° C
  3. additionA further 700 ml of benzene are added
  4. customthe mixture is evaporated under the same conditions
  5. customIt is recrystallised in diethyl ether
  6. customdried at 60° C.
  7. customrecrystallised twice in ethanol
  8. additiontreating it with vegetable charcoal
  9. customduring the first recrystallisation
  10. washwashed with diethyl ether
  11. customdried at 80° C

Sources & evidence

ORD record
ord-7aa1866aed524b8f80914bed9192448a
Source dataset
uspto-grants-1993_03
Patent number
US05192797

Reaction notes

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