Hydrochloric Acid → HCID 21960048, compound

HRID 1377290Notes

Reaction equation

HRID 1377290 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]4C(=O)C5=CC=CC=C5C4=O)[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.O.NN.[ClH:35]>CO.O.C(O)C>[ClH:35].[ClH:35].[NH2:19][CH2:18][CH2:17][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][CH:9]([C:6]2[C:5]3[CH:30]=[CH:31][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:10][CH2:11]1

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 24654Hydrazine hydrate (1:1)HCID 15816944HCID 15816944, compound

Product 1

HCID 21960048HCID 21960048, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of N-[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl) piperidinyl]-butyl]phthalimide (6.9 g, 16.4 mmol) and hydrazine monohydrate (1.64 g, 32.8 mmol) in methanol (70 ml) was heated at reflux for 3 hours. At the end of the reaction, methanol was removed to leave a crude solid. This was dissolved in water and acidified with HCl to pH 2. The insolubles were filtered. The aqueous solution was basified with 50% NaOH, and then extracted with dichloromethane. The dichloromethane solution was washed with water and brine, and then dried over MgSO4. The solvent was removed to a colorless oil: 4.48 g. This oil was treated with 2.5 equivalents of HCl in ethanol. The solid was collected. Recrystallization from ethanol (65 ml) and methanol (20 ml) gave 2.0 g of 1-(4-aminobutyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine dihydrochloride as white crystals, m.p.=234°-237° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customwas removed
  4. customto leave a crude solid
  5. filtrationThe insolubles were filtered
  6. extractionextracted with dichloromethane
  7. washThe dichloromethane solution was washed with water and brine
  8. dry with materialdried over MgSO4
  9. customThe solvent was removed to a colorless oil
  10. customThe solid was collected
  11. customRecrystallization from ethanol (65 ml) and methanol (20 ml)

Sources & evidence

ORD record
ord-2d002d27924541a4906b5ebce2c65d33
Source dataset
uspto-grants-1997_09
Patent number
US05663449

Reaction notes

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