3-(Trifluoromethyl)phenol → HCID 131718543, compound

HRID 1728655Notes

Reaction equation

HRID 1728655 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=2)[CH:7]([CH2:20][Cl:21])[CH2:6]1)[CH2:2][CH2:3][CH3:4].[F:22][C:23]([F:32])([F:31])[C:24]1[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=1.[H-].[Na+]>C(N1CCC(C2C=CC(N(C)C)=CC=2)C(CO)C1)CCC.CN(C=O)C>[ClH:21].[CH2:1]([N:5]1[CH2:10][CH2:9][C@@H:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=2)[C@H:7]([CH2:20][O:30][C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([C:23]([F:22])([F:31])[F:32])[CH:25]=2)[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydrideHCID 53871722HCID 53871722, compound

Product 1

HCID 131718543HCID 131718543, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 19014393HCID 19014393, compoundSolvent2×

Procedure

0.4 g of 1-butyl-3-chloromethyl-4-(4-dimethylaminophenyl) piperidine (18) in DMF (25 ml) (prepared from compound (12) by known procedures) was added to a 70° C. hot mixture of 3-trifluoromethylphenol (0.28 g) and NaH (0.09 g) in DMF (25 ml). Reaction time 2 h at 100° C. Evaporation with 3×100 ml toluene. The residue was extracted with NaOH (4N)-ether, the etheral layer separated and dried (MgSO4), purified on a silica gel column and precipitated with concentrated HCl from acetone. Yield 0.22 g of colorless crystals. M.p. 221°-223° C.

Workup

  1. customReaction time 2 h at 100° C
  2. customEvaporation with 3×100 ml toluene
  3. extractionThe residue was extracted with NaOH (4N)-ether
  4. customthe etheral layer separated
  5. dry with materialdried (MgSO4)
  6. custompurified on a silica gel column
  7. customprecipitated with concentrated HCl from acetone

Sources & evidence

ORD record
ord-3f5990dfba61446cb29e59fce51aef7f
Source dataset
uspto-grants-1994_07
Patent number
US05328917

Reaction notes

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