Ammonium Chloride → HCID 15117210, compound

HRID 1029608Notes

Reaction equation

HRID 1029608 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Li])CCC.[C:12]([N:15]1[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]1)(=[O:14])[CH3:13].[Cl-].[NH4+]>O1CCCC1.CCCCCC.C(OCC)(=O)C.C(O)(=O)C>[C:12]([N:15]1[CH2:20][CH2:19][C:18]([OH:21])([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH2:17][CH2:16]1)(=[O:14])[CH3:13]

Participants

9

Reactant 4

HCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 122563N-Acetyl-4-piperidoneHCID 178418339Butyllithium

Product 1

HCID 15117210HCID 15117210, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of trimethylsilylacetylene (17 ml) in tetrahydrofuran (100 ml) were added successively a solution of n-butyllithium in n-hexane (1.50M, 81 ml) and a solution of 1-acetyl-4-piperidone (11.5 g) in tetrahydrofuran (15 ml) at -78° C. After stirring at -78° C. for 30 minutes, to the mixture was added acetic acid (5.0 ml) and the resultant mixture was taken up into a mixture of aqueous ammonium chloride (300 ml) and ethyl acetate (300 ml) at 0° C. The organic layer was separated and washed with brine, dried over magnesium sulfate. Evaporation of the solvent gave a crystalline which was collected by filtration, and washed with n-hexane to give 1-acetyl-4-hydroxy-4-(2-trimethylsilylethynyl)piperidine (14.48 g).

Workup

  1. customat -78° C
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave a crystalline which
  7. filtrationwas collected by filtration
  8. washwashed with n-hexane

Sources & evidence

ORD record
ord-369233bfd6a74cafa7748343c80287a6
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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