Trifluoroacetic acid → HCID 23343663, compound

HRID 2419034Notes

Reaction equation

HRID 2419034 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2(O)[C:14]3[CH:15]=[C:16]([I:19])[CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]2=3)[CH2:4][CH2:3]1.FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>>[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[C:16]([I:19])[CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]2=3)[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 203168533-Iodo-5-(1-methyl-4-piperidinyl)-5H-dibenzo[a,d]cyclohepten-5-ol

Product 1

HCID 23343663HCID 23343663, compound

Procedure

A solution of 3.23 g. of 1-methyl-4-(3-iodo-5-hydroxy-5H-dibenzo[a,d]cyclohepten-5-yl)piperidine, 30 ml. of trifluoroacetic acid and 10 ml. of trifluoroacetic anhydride is refluxed for 6 hours. The solution is concentrated on a rotary evaporator and the residue is made basic with 5% sodium hydroxide solution. The oil that precipitates is extracted into ether, and this ether phase is washed with water, dried over magnesium sulfate, filtered, and the ether removed on a rotary evaporator. The residue is triturated with acetonitrile, collected and dried to give 2.36 g. of material. This material is recrystallized from ether acetate to give pure (±)-1-methyl-4-(3-iodo-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine, m.p. 166°-170°.

Workup

  1. concentrationThe solution is concentrated on a rotary evaporator
  2. customThe oil that precipitates
  3. extractionis extracted into ether
  4. washthis ether phase is washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe ether removed on a rotary evaporator
  8. customThe residue is triturated with acetonitrile
  9. customcollected
  10. customdried
  11. customto give 2.36 g
  12. customThis material is recrystallized from ether acetate

Sources & evidence

ORD record
ord-7faa2df54ae0416fa3997ca1f1c53d05
Source dataset
uspto-grants-1978_08
Patent number
US04104398

Reaction notes

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