Trifluoroacetic acid → HCID 19784379, compound

HRID 257089Notes

Reaction equation

HRID 257089 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].C(O)(=O)/C=C/C(O)=O.O[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][CH:29]([N:32]([CH3:41])[CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:28][CH2:27]2)=[CH:22][CH:21]=1)[CH3:19].C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[OH-].[Na+]>O>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH2:18]([C:20]1[CH:21]=[CH:22][C:23]([N:26]2[CH2:27][CH2:28][CH:29]([N:32]([CH3:41])[CH2:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:30][CH2:31]2)=[CH:24][CH:25]=1)[CH3:19]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 67854747HCID 67854747, compound

Product 1

HCID 19784379HCID 19784379, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5.1 g (15 mmol) of the product from Example 13, 2.6 g (22.5 mmol) of triethylsilane and 17.1 g (15 mmol) of trifluoroacetic acid was heated at 60° C. for 2 hours. The mixture was then poured into water, made alkaline with 4M sodium hydroxide solution and extracted with methylene chloride. The organic phase was separated off, dried and evaporated in a rotary evaporator. The resulting residue was purifed by chromatography on silica gel (eluent: toluene/acetone=2/1). The oily product crystallized as the fumarate. 1.5 g of 1-(4-ethylphenyl)-4-(N-methyl-N-(2-phenylethyl)amino)piperidine fumarate were obtained. Melting point 163°-165° C.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic phase was separated off
  3. customdried
  4. customevaporated in a rotary evaporator
  5. customThe oily product crystallized as the fumarate

Sources & evidence

ORD record
ord-d971b3e909c249479908159fae04b489
Source dataset
uspto-grants-1993_11
Patent number
US05260318

Reaction notes

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