Tetrabutylammonium Fluoride → HCID 22314197, compound

HRID 347205Notes

Reaction equation

HRID 347205 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]([CH2:36][CH3:37])[CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:35]=[CH:34][C:18]2[C:19]([C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:24][CH:23]=3)=[N:20][S:21][C:17]=2[CH:16]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:36]([N:9]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:35]=[CH:34][C:18]2[C:19]([C:22]3[CH:23]=[CH:24][C:25]([N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:26][CH:27]=3)=[N:20][S:21][C:17]=2[CH:16]=1)[CH2:8][CH2:7][OH:6])[CH3:37]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22313981HCID 22313981, compound

Product 1

HCID 22314197HCID 22314197, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

220 mg (0.39 mmol) [2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-ethyl-{4-[3-(4-piperidin-1-yl-phenyl)-benzo[d]isothiazol-6-yloxy]-butyl}-amine in 5 ml THF were treated with 0.6 ml 1M TBAF in THF for 1 h at RT. The solution was concentrated and the crude product subjected to column chromatography on silica gel with CH2Cl2:MeOH 9:1 to give 146 mg (83%) 2-(Ethyl-{4-[3-(4-piperidin-1-yl-phenyl)-benzo[d]isothiazol-6-yloxy]-butyl}-amino)-ethanol as yellow oil, MS: 454 (MH+).

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-f63b4e211ff3404abda5abbc99f3598f
Source dataset
uspto-grants-2007_02
Patent number
US07173043B2

Reaction notes

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