Tetrabutylammonium Fluoride → HCID 22277246, compound

HRID 1063865Notes

Reaction equation

HRID 1063865 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[C:13]2[O:17][CH:16]=[CH:15][C:14]=2[CH:18]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:8][CH2:9][C:10]1[CH:11]=[C:12]([N:19]2[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]2)[C:13]2[O:17][CH:16]=[CH:15][C:14]=2[CH:18]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22277394HCID 22277394, compound

Product 1

HCID 22277246HCID 22277246, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.42 gm 1-(5-(tert-butyldimethylsilyloxymethyl)benzofur-7-yl)-4-tert-butoxycarbonylpiperazine and excess tetrabutylammonium fluoride was stirred in tetrahydrofuran for 30 minutes. The reaction mixture was then diluted with ethyl acetate and washed three times with dilute aqueous sodium bicarbonate. The remaining organics were dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 5:2 hexane:ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 0.28 gm (89%) 1-(5-(hydroxymethyl)benzofur-7-yl)-4-tert-butoxycarbonylpiperazine. This material was dissolved in trifluoroacetic acid and the resulting solution stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue subjected to silica gel chromatography, eluting with dichloromethane containing 10% methanol and a trace of ammonia. Fractions containing product were combined and concentrated under reduced pressure to provide 1-(5-hydroxymethyl)benzofur-7-yl)piperazine. This compound was treated with hydrogen chloride to provide the title compound as a white solid.

Workup

  1. washwashed three times with dilute aqueous sodium bicarbonate
  2. dry with materialThe remaining organics were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washeluting with 5:2 hexane
  5. additionFractions containing product
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d1a5fa269156406087852817ca459bd8
Source dataset
uspto-grants-2005_11
Patent number
US06967201B1

Reaction notes

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