Methanol → HCID 15681286, compound

HRID 1493196Notes

Reaction equation

HRID 1493196 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:5][CH2:4]1)#N.[H-].C([Al+]CC(C)C)C(C)C.C[OH:28].O>C1(C)C=CC=CC=1.CCCCCC>[C:11]1([CH2:10][CH2:9][N:6]2[CH2:7][CH2:8][CH:3]([CH:1]=[O:28])[CH2:4][CH2:5]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14257836HCID 14257836, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 15681286HCID 15681286, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4-cyano-1-(2-phenylethyl)piperidine (6.5 g, 30.3 mmol) in dry toluene (100 ml) cooled in an ice bath was added dropwise 43 ml (43 mmol) of 1M diisobutylaluminum hydride in hexane. After the addition was complete, the mixture was warmed to room temperature and stirred overnight (16 h). Methanol was added to decompose any unreacted reagent and H2O was added with vigorous stirring. The gelatinous aluminum salts were removed by filtration through Celite and the filtrate extracted with toluene (2×100 ml). The extracts were combined, washed with saturated aqueous NaCl, dried (MgSO4) filtered and evaporated to give a clear oil. This oil was flash chromatographed on silica gel using acetone as eluent to give product as a clear oil, which was used without further purification.

Workup

  1. additionAfter the addition
  2. additionwas added with vigorous stirring
  3. customThe gelatinous aluminum salts were removed by filtration through Celite
  4. extractionthe filtrate extracted with toluene (2×100 ml)
  5. washwashed with saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto give a clear oil
  10. customchromatographed on silica gel
  11. customto give product as a clear oil, which
  12. customwas used without further purification

Sources & evidence

ORD record
ord-2fe5b23a3bd745bd915332cc3fc2e52a
Source dataset
uspto-grants-1991_06
Patent number
US05021428

Reaction notes

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