Hydrochloric Acid → HCID 21960048, compound

HRID 1601242Notes

Reaction equation

HRID 1601242 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 mdxture 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. temperatureat reflux for 3 hours
  2. customwas removed
  3. customto leave a crude solid
  4. filtrationThe insolubles were filtered
  5. extractionextracted with dichloromethane
  6. washThe dichloromethane solution was washed with water and brine
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed to a colorless oil
  9. customThe solid was collected
  10. customRecrystallization from ethanol (65 ml) and methanol (20 ml)

Sources & evidence

ORD record
ord-d0432c4cb3ee4f39a33d4b1fee0e97e2
Source dataset
uspto-grants-1999_11
Patent number
US05977113

Reaction notes

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