Hydrochloric Acid → HCID 86594081, compound

HRID 348541Notes

Reaction equation

HRID 348541 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C@@H:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]3[OH:17])[CH2:7][CH2:6]2)[O:4]CC1.Cl.O.[OH-].[Na+]>O1CCOCC1>[OH:17][C@@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]1[N:8]1[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86594080HCID 86594080, compound

Product 1

HCID 86594081HCID 86594081, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

A solution of (+/−)-trans-2-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-cyclohexanol (1.50 g, 6.25 mmol) in dioxane (45 ml) was treated with 5N hydrogen chloride (10 ml). The mixture was warmed to 105° C. and stirred for 4 h. After cooling to room temperature, water (9 ml) was added to the mixture, which was then basified to pH 14 by slow addition of 5N sodium hydroxide. The mixture was then extracted three times with ethyl acetate and the combined organic extracts were dried with anhydrous sodium sulphate and concentrated. The residual oil was purified by flash chromatography on silica gel, eluting with methanol 0–5% in dichloromethane. (+/−)-trans-1-(2-Hydroxy-cyclohexyl)-piperidin-4-one (0.830 g, 68%) was obtained as a white solid, MS (ISP): m/e=198.3 (M+H+).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe mixture was then extracted three times with ethyl acetate
  3. dry with materialthe combined organic extracts were dried with anhydrous sodium sulphate
  4. concentrationconcentrated
  5. customThe residual oil was purified by flash chromatography on silica gel
  6. washeluting with methanol 0–5% in dichloromethane

Sources & evidence

ORD record
ord-afdd071fffdf4f648476ffd5265e98e7
Source dataset
uspto-grants-2007_02
Patent number
US07176316B2

Reaction notes

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