Sodium Hydroxide → HCID 21959997, compound

HRID 1420359Notes

Reaction equation

HRID 1420359 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]4[CH:20]=[C:21]([NH:25]C(=O)C)[CH:22]=[CH:23][CH:24]=4)[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[OH-].[Na+]>Cl>[F:1][C:2]1[CH:30]=[CH:29][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]4[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=4)[NH2:25])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21959998N-[3-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]phenyl]acetamide

Product 1

HCID 21959997HCID 21959997, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of N-[3-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidiny]propoxyl]phenyl]acetamide (9.2 g, 22 mmol), prepared as described in the previous example, in 15% hydrochloric acid (110 ml) was heated at 100° C. for 2.5 hours until a homogeneous solution resulted. The reaction was cooled to 0° C. in an ice bath and basified with 50% NaOH. The product was extracted with ethyl acetate (3×200 ml). The ethyl acetate solution was washed with water, brine, then dried over Na2SO4. The solvent was removed. The crude product was purified on a flash chromatography column. The product thus obtained was a solid: 6.6 g (80%). Recrystallization from hot ethanol (50 ml) gave 3-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-aniline as off-white crystals: 3.46 g, m.p.=115°-117° C.

Workup

  1. customprepared
  2. customresulted
  3. temperatureThe reaction was cooled to 0° C. in an ice bath
  4. extractionThe product was extracted with ethyl acetate (3×200 ml)
  5. washThe ethyl acetate solution was washed with water, brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed
  8. customThe crude product was purified on a flash chromatography column
  9. customThe product thus obtained
  10. customRecrystallization from hot ethanol (50 ml)

Sources & evidence

ORD record
ord-047cc20990f4455d9a982573d564972b
Source dataset
uspto-grants-1999_03
Patent number
US05889035

Reaction notes

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