Water → 1-[4,4-Bis(4-fluorophenyl)butyl]-4-methylaminopiperidine

HRID 2073493Notes

Reaction equation

HRID 2073493 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19](OCC)=O)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([NH:18][CH3:19])[CH2:16][CH2:17]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 138832851-[4,4-Bis(4-fluorophenyl)butyl]-4-ethoxycarbonylaminopiperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 198571831-[4,4-Bis(4-fluorophenyl)butyl]-4-methylaminopiperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

13.0 g (31.3 mmol) of 1-[4,4-bis(4-fluorophenyl)butyl]-4-ethoxycarbonylaminopiperidine were dissolved in 60 ml of absolute tetrahydrofuran, the solution was added dropwise to a suspension of 1.82 g (46.9 mmol) of LiAlH4 in 60 ml of absolute tetrahydrofuran and the mixture was stirred at room temperature for 1 hour and at 40° C. for 1 hour. 1.8 ml of H2O, 1.8 ml of 2N NaOH and a further 9 ml of H2O were added dropwise in succession, with cooling; the precipitate formed was then filtered off with suction and rinsed with a little tetrahydrofuran and the filtrate was dried and concentrated.

Workup

  1. temperaturewith cooling
  2. customthe precipitate formed
  3. filtrationwas then filtered off with suction
  4. washrinsed with a little tetrahydrofuran
  5. customthe filtrate was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-204f6f57db8241ef975fa2817a62fb0e
Source dataset
uspto-grants-1990_04
Patent number
US04918073

Reaction notes

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