Hydrochloric Acid → HCID 20453410, compound

HRID 1948597Notes

Reaction equation

HRID 1948597 reaction equation
Cl.[CH3:2][NH:3][C:4]1([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH2:6][CH2:5]1>O>[CH3:2][NH:3][C:4]1([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][C:7](=[O:8])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12595584HCID 12595584, compound

Product 1

HCID 20453410HCID 20453410, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of conc. HCl (15 ml) and water (8 ml) was added to N-methyl-8-(thiophen-2-yl)-1,4-dioxaspiro[4.5]decan-8-amine (2 g, 7.9 mmole) and stirred for 5 days at RT. The reaction mixture was worked up by dilution with water (30 ml) and extraction with ether. The ethereal phase was discarded. The aqueous phase was then made alkaline with 2N NaOH and extracted with dichloromethane (3×30 ml). The organic phase thereby obtained was dried over Na2SO4 and then concentrated by evaporation on a rotary evaporator. The residue was purified by column chromatography (silica gel 60 (50 g); 500 ml ethyl acetate/ethanol (5:1)] and Ket-4 was obtained in a yield of 1.4 g (85%) as a solid with a melting point of 72°-74° C.

Workup

  1. extractionThe reaction mixture was worked up by dilution with water (30 ml) and extraction with ether
  2. extractionextracted with dichloromethane (3×30 ml)
  3. customThe organic phase thereby obtained
  4. dry with materialwas dried over Na2SO4
  5. concentrationconcentrated by evaporation on a rotary evaporator
  6. customThe residue was purified by column chromatography (silica gel 60 (50 g)
  7. custom500 ml ethyl acetate/ethanol (5:1)] and Ket-4 was obtained in a yield of 1.4 g (85%) as a solid with a melting point of 72°-74° C.

Sources & evidence

ORD record
ord-4a9cb89bfa264065b52b742ad994c529
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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