Hydrochloric Acid → 2H-Pyran-4-ol, 4-[[4-(aminomethyl)-1-piperidinyl]methyl]tetrahydro-

HRID 2425748Notes

Reaction equation

HRID 2425748 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2([OH:22])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH2:11][CH2:10]1)(C)(C)C.Cl.O1CCOCC1>CO>[NH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2([OH:22])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59255059tert-butyl({1-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidin-4-yl}methyl)carbamate

Product 1

HCID 592550572H-Pyran-4-ol, 4-[[4-(aminomethyl)-1-piperidinyl]methyl]tetrahydro-Yield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl({1-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidin-4-yl}methyl)carbamate (50.28 g, 153 mmol, step 1) in methanol was added 4N hydrogen chloride in dioxane (200 mL, 800 mmol) at room temperature. After 4 h, the volatile materials were removed by evaporation. The resulting amorphous was precipitated with diethyl ether/methanol (5:1). The precipitate was collected and added to the ice cooled 6N aqueous sodium hydroxide (200 mL) gradually. The mixture was extracted with dichloromethane/methanol (10:1, 500 mL×4). The combined organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give 24.90 g (99%) of the title compound as a pale brown amorphous.

Workup

  1. customthe volatile materials were removed by evaporation
  2. customThe resulting amorphous was precipitated with diethyl ether/methanol (5:1)
  3. customThe precipitate was collected
  4. additionadded to the ice
  5. temperaturecooled 6N aqueous sodium hydroxide (200 mL) gradually
  6. extractionThe mixture was extracted with dichloromethane/methanol (10:1, 500 mL×4)
  7. washThe combined organic phase was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e34e7d857e22483fabd131ca80e4da44
Source dataset
uspto-grants-2011_06
Patent number
US07964727B2

Reaction notes

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