128396-57-6 → HCID 15068036, compound

HRID 1031934Notes

Reaction equation

HRID 1031934 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[C:29](=[O:30])[CH2:28][C:23]4([CH2:27][CH2:26][CH2:25][CH2:24]4)[CH:22]([OH:31])[C:21]3=[O:32])[CH2:12][CH2:11]2)=[N:2]1>C(#N)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([CH:22]3[O:31][C:29](=[O:30])[CH2:28][C:23]43[CH2:27][CH2:26][CH2:25][CH2:24]4)=[O:32])[CH2:12][CH2:11]2)=[N:2]1

Participants

3

Reactant 1

HCID 15068025128396-57-6

Product 1

HCID 15068036HCID 15068036, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 8-[4-[4-(1,2-benzisothiazol-3 yl)-1piperazinyl]butyl]-6-hydroxy-8-azaspiro[4.5]decane-7,9dione (1.14 g, 2.5 mmol) and KF-Al2O3 (0.36 g, ~1 equiv) in acetonitrile (25 mL) was vigorously stirred at room temperature under Ar for 4 h. The supernatant was then decanted and replaced with fresh acetonitrile (25 mL), and stirring was continued for 4 h. This process was repeated until the residue contained no more starting material (5× in total). The combined supernatants were evaporated and the resulting gum was purified by flash chromatography (EtOAc, then EtOAc acetone (1:1) to give the title compound (0.75 g, 66%) as an off-white foam. A 650 mg sample of the title compound was dissolved in excess ethanolic HCl and the solution was evaporated to dryness. The residue was taken up in acetone, ether was added and the resulting solid was collected and dried in vacuo to give 620 mg of a cream-colored powder, m.p. 194-197° C. An analytical sample was prepared by trituration with acetone to give the hydrochloride as a white powder; IR (CH2Cl2) 3430, 1785, 1680 cm-1 ; 1H NMR (CDCl3) δ 7.86-7.80 (m, 2H), 7.54-7.36 (m, 2H), 7.29 (b s, 1H), 4.77 (s, 1H), 4.12-4.08 (m, 4H), 3.56-3.50 (m, 2H), 3.47-3.33 (m, 2H), 3.14-3.04 (m, 4H), 2.62, 2.37 (q, J=17.1 Hz, 2H), 2.1-1.4 (b m, 13H); Anal. calcd for C24H32N4O3S/1.4 HCl:

Workup

  1. customThe supernatant was then decanted
  2. stirringstirring
  3. waitwas continued for 4 h
  4. customThe combined supernatants were evaporated
  5. customthe resulting gum was purified by flash chromatography (EtOAc

Sources & evidence

ORD record
ord-fc2c61fc796b47c0b46866be9643ca95
Source dataset
uspto-grants-1990_09
Patent number
US04956368

Reaction notes

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