Hydrochloric Acid → Ethyl [3-[5-(naphthalen-1-yl)-1,3-dioxan-2-yl]propyl]carbamate

HRID 1613335Notes

Reaction equation

HRID 1613335 reaction equation
Cl.N[CH:3]([CH3:21])[CH2:4][CH:5]1[O:10][CH2:9][CH:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)[CH2:7][O:6]1.C([N:24](CC)CC)C.Cl[C:30]([O:32][CH2:33][CH3:34])=[O:31].Cl>ClCCl>[C:11]1([CH:8]2[CH2:9][O:10][CH:5]([CH2:4][CH2:3][CH2:21][NH:24][C:30](=[O:31])[O:32][CH2:33][CH3:34])[O:6][CH2:7]2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 197757382-Aminopropyl-5-(naphthalen-1-yl)-1,3-dioxane hydrochloride

Product 1

HCID 54349423Ethyl [3-[5-(naphthalen-1-yl)-1,3-dioxan-2-yl]propyl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4 g (13 mmol) of 2-aminopropyl-5-(naphthalen-1-yl)-1,3-dioxane hydrochloride are stirred at ambient temperature for 10 min. with 4 ml of triethylamine in 200 ml of dichloromethane, 1.4 g (13 mmol) of ethyl chloroformate in 20 ml of dichloromethane are then added, drop by drop, and the mixture is stirred at ambient temperature for 3 h. Dilute hydrochloric acid is added, and the organic phase is separated, washed with water and with a saturated solution of sodium hydrogen carbonate, dried over magnesium sulphate, filtered and evaporated to dryness. An oil is obtained which crystallises in pentane; the solid is filtered and purified by chromatography on a silica gel column eluted with ethyl acetate. 2.4 g (7 mmol) of product are finally isolated.

Workup

  1. additionare then added
  2. customthe organic phase is separated
  3. washwashed with water and with a saturated solution of sodium hydrogen carbonate
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customAn oil is obtained which
  8. customcrystallises in pentane
  9. filtrationthe solid is filtered
  10. custompurified by chromatography on a silica gel column
  11. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-ed622b47cf1544c68d8a891715e958f8
Source dataset
uspto-grants-1993_03
Patent number
US05192797

Reaction notes

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