Ethanaminium, N,N,N-triethyl-, fluoride (1:1) → HCID 59382870, compound

HRID 1254197Notes

Reaction equation

HRID 1254197 reaction equation
[CH:1]1([C:4]#[C:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH:12]([O:28][CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:13]2[CH2:18][CH2:17][CH2:16][N:15](S(CC[Si](C)(C)C)(=O)=O)[CH2:14]2)[CH2:3][CH2:2]1.[F-].C([N+](CC)(CC)CC)C>C(#N)C>[CH3:33][O:32][CH2:31][CH2:30][CH2:29][O:28][CH:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:5]#[C:4][CH:1]1[CH2:2][CH2:3]1)[CH:13]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]1

Participants

4

Reactant 2

HCID 69582Ethanaminium, N,N,N-triethyl-, fluoride (1:1)HCID 59382940HCID 59382940, compound

Product 1

HCID 59382870HCID 59382870, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A 50-mL round bottom flask was charged with 3-((2-(cyclopropylethynyl)phenyl)(3-methoxypropoxy)methyl)-1-(2-(trimethylsilyl)ethylsulfonyl)piperidine (63 mg, 0.128 mmol, 1.0 equiv), tetraethylammonium fluoride (63 mg, 0.422 mmol, 3.4 equiv) and acetonitrile (5 mL). The mixture was heated to 65° C. for 17 h. Analysis of the yellow reaction mixture by LC-MS showed consumption of the protected piperidine and formation of a new signal containing the mass of the desired product. The acetonitrile was removed under reduced pressure and the residue was partitioned between CH2Cl2 and water. The layers were separated and the aqueous layer was extracted twice with additional CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and evaporated, yielding 3-((3-methoxypropoxy)(2-(2-cyclopropylethynyl)phenyl)methyl)piperidine (40 mg, 95%). No additional purification was attempted. MS ESI +ve m/z 328 (M+H+).

Workup

  1. customconsumption of the protected piperidine and formation of a new signal
  2. additioncontaining the mass of the desired product
  3. customThe acetonitrile was removed under reduced pressure
  4. customthe residue was partitioned between CH2Cl2 and water
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted twice with additional CH2Cl2
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-a2cc1e73446e4fde85444d7b271c086e
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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