Methanol → HCID 9975721, compound

HRID 487135Notes

Reaction equation

HRID 487135 reaction equation
CCCCCC.[H-].C([Al+]CC(C)C)C(C)C.[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[O:25][CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][CH:31]([C:34]#N)[CH2:30][CH2:29]2)=[CH:20][CH:19]=1.[Cl-].[NH4+].C[OH:46]>O1CCCC1>[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[O:25][CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][CH:31]([CH:34]=[O:46])[CH2:30][CH2:29]2)=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 104509191-[2-Bis(4-fluorophenyl)methoxyethyl]-4-piperidinecarbonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 9975721HCID 9975721, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1(a) 75 ml of a 1M hexane solution containing diisobutylaluminum hydride were added to 400 ml of tetrahydrofuran under a stream of nitrogen, and the mixture was cooled at -78° C. Whilst the mixture's internal temperature was -15° C., 20.25 g of 1-[2-bis(4-fluorophenyl)methoxyethyl]-4-piperidinecarbonitrile (prepared as described in Preparation 4) were added to the mixture over a period of 40 minutes, and the resulting mixture was stirred for 30 minutes at -15° C. The mixture was then allowed to stand overnight at room temperature. At the end of this time, the mixture was placed in an ice bath, and 15 ml of methanol, followed by 100 ml of a saturated aqueous solution of ammonium chloride, were added. The reaction mixture was then extracted with ethyl acetate. The extract was purified by silica gel column chromatography. Elution with 3% by volume methanol in methylene chloride afforded 14.67 g (yield 72%) of the title compound as an oily substance.

Workup

  1. customwas -15° C.
  2. waitto stand overnight at room temperature
  3. customAt the end of this time, the mixture was placed in an ice bath
  4. additionwere added
  5. extractionThe reaction mixture was then extracted with ethyl acetate
  6. customThe extract was purified by silica gel column chromatography
  7. washElution with 3% by volume methanol in methylene chloride

Sources & evidence

ORD record
ord-8f98132156584604b10ff88d19a1c6d7
Source dataset
uspto-grants-1994_03
Patent number
US05294623

Reaction notes

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