Potassium borohydride → HCID 20463229, compound

HRID 325967Notes

Reaction equation

HRID 325967 reaction equation
Cl.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[O:23])[CH2:15][CH2:14]1.C[O-].[Na+].[BH4-].[K+]>CO>[F:30][C:27]1[CH:26]=[CH:25][C:24]([CH:22]([OH:23])[CH2:21][CH2:20][CH2:19][N:16]2[CH2:15][CH2:14][CH:13]([O:12][C:3]3[CH:4]=[CH:5][C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH:2]=3)[CH2:18][CH2:17]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 4192641Potassium borohydrideHCID 10942334Sodium MethoxideHCID 20463195HCID 20463195, compound

Product 1

HCID 20463229HCID 20463229, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 8.0 g (0.02 mole) of 4-[4-(2-naphthalenyloxy)-1-piperidyl]-1-(4-fluorophenyl)-1-butanone HCl in 50 ml of methanol is added 1.1 g (0.02 mole) of sodium methoxide and then 2.7 g (0.05 mole) of potassium borohydride and the mixture stirred at room temperature for 2 hours. The methanol is removed at reduced pressure on a steam bath after which 50 ml of 10% sodium hydroxide solution is added. The mixture is stirred for 15 minutes and 100 ml of chloroform is added. Stirring is continued for 1/2 hour. The chloroform layer is separated and combined with two 25 ml chloroform extracts of the aqueous phase, washed with water and with brine, dried over MgSO4, filtered and concentrated to a solid. The solid material is recrystallized from ethanol/water to give α-(4-fluorophenyl)-4-(2-naphthalenyloxy)-1-piperidinebutanol.

Workup

  1. customThe methanol is removed at reduced pressure on a steam bath after which 50 ml of 10% sodium hydroxide solution
  2. additionis added
  3. addition100 ml of chloroform is added
  4. stirringStirring
  5. waitis continued for 1/2 hour
  6. customThe chloroform layer is separated
  7. washwashed with water and with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated to a solid
  11. customThe solid material is recrystallized from ethanol/water

Sources & evidence

ORD record
ord-95f03b360d304eb78dbec8de5c49c808
Source dataset
uspto-grants-1984_04
Patent number
US04443462

Reaction notes

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