Sodium borohydride → HCID 14257858, compound

HRID 1165864Notes

Reaction equation

HRID 1165864 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)=[O:16])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=3)[OH:16])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14257846HCID 14257846, compound

Product 1

HCID 14257858HCID 14257858, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [1-(2-phenylethyl)-4-piperidinyl][3-(trifluoromethyl)-phenyl]-methanone (2.8 g, 7.75 mmol) in methanol (50 ml) cooled in an ice bath was added portionwise sodium borohydride (0.3 g, 7.75 mmol). The reaction was allowed to warm to room temperature and stirred an additional 4 h. The mixture was evaporated and the residue extracted with Et2O, washed with H2O (3×100 ml), saturated aqueous NaCl (1×100 ml), dried (Mg SO4), filtered and evaporated to give a white solid. This solid was recrystallized from ether-hexane to give white needles, mp 143°-147° C.

Workup

  1. customThe mixture was evaporated
  2. extractionthe residue extracted with Et2O
  3. washwashed with H2O (3×100 ml), saturated aqueous NaCl (1×100 ml)
  4. dry with materialdried (Mg SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a white solid
  8. customThis solid was recrystallized from ether-hexane
  9. customto give white needles, mp 143°-147° C.

Sources & evidence

ORD record
ord-a200fa468f024c46924ae14227302b4d
Source dataset
uspto-grants-1990_03
Patent number
US04912117

Reaction notes

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