Acetic Acid → 6-chloro-2,3-dihydro-1-hydroxy-3-oxo-2-[1-[[3-(trifluoromethyl)phenyl]methyl]-4-piperidinyl]-1H-isoindole-5-sulfonamide

HRID 745839Notes

Reaction equation

HRID 745839 reaction equation
O=C1C2C(=CC=CC=2)C(=O)N1.[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17](=[O:40])[N:18]([CH:23]3[CH2:28][CH2:27][N:26]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=4)[CH2:25][CH2:24]3)[C:19]2=[O:22])=[CH:15][C:14]=1[S:41]([NH2:44])(=[O:43])=[O:42].C(O)(=O)C>C(OCC)(=O)C>[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17](=[O:40])[N:18]([CH:23]3[CH2:24][CH2:25][N:26]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:38])([F:37])[F:39])[CH:31]=4)[CH2:27][CH2:28]3)[CH:19]2[OH:22])=[CH:15][C:14]=1[S:41]([NH2:44])(=[O:43])=[O:42]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6809PhthalimideHCID 233124416-Chloro-2,3-dihydro-1,3-dioxo-2-[1-[[3-(trifluoromethyl)-phenyl]methyl]-4-piperidinyl]-1H-isoindole-5-sulfonamide

Product 1

HCID 133706196-chloro-2,3-dihydro-1-hydroxy-3-oxo-2-[1-[[3-(trifluoromethyl)phenyl]methyl]-4-piperidinyl]-1H-isoindole-5-sulfonamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the 1,3-dioxoisoindole of part (a), (8.1 g., 0.0161 mole), zinc dust (5.78 g., 0.088 mole) and 150 ml. of acetic acid was stirred for 0.5 hr. at 50°-70°, cooled. Residual material, obtained by concentration of the filtrate in vacuo, was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution and the aqueous layer re-extracted with ethyl acetate. Combined extracts were washed with saturated sodium bicarbonate, dried (MgSO4) and concentrated in vacuo. Trituration of the residue with ethyl acetate provided 6-chloro-2,3-dihydro-1-hydroxy-3-oxo-2-[1-[[3-(trifluoromethyl)phenyl]methyl]-4-piperidinyl]-1H-isoindole-5-sulfonamide as a white solid, m.p. 204°-205°.

Workup

  1. temperatureat 50°-70°, cooled
  2. customResidual material, obtained by concentration of the filtrate in vacuo
  3. washwashed with saturated sodium bicarbonate solution
  4. extractionthe aqueous layer re-extracted with ethyl acetate
  5. washCombined extracts were washed with saturated sodium bicarbonate
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f42b402a5e44adaa85c914c03eb7664
Source dataset
uspto-grants-1986_07
Patent number
US04600758

Reaction notes

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