Hydrochloric Acid → HCID 131718780, compound

HRID 2379978Notes

Reaction equation

HRID 2379978 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16]C4C=CC=C5C(NC(=O)C=45)=O)[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.O.[NH2:31]N.Cl.[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38]>CO.C(O)C.O>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38].[F:1][C:2]1[CH:29]=[CH:28][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][NH2:31])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1.[F:1][C:2]1[CH:29]=[CH:28][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][NH2:31])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 444972Fumaric AcidHCID 21960093HCID 21960093, compound

Product 1

HCID 131718780HCID 131718780, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl phthalimide (4.6 in, 11.7 mmol) and hydrazine monohydrate (1.17 gm, 23.4 mmol) in methanol (50 ml) was heated at reflux overnight. At the end of the reaction, methanol was removed to leave a crude solid. This was stirred with water (150 ml) and acidified with HCl to pH=2. The insolubles were filtered. The aqueous solution was basified with 50% NaOH then extracted with DCM (2×250 ml). The DCM solution was washed with brine and dried over MgSO4. The solvent was removed to produce a colorless oil: 2.12 gm. This oil was treated with a solution of fumaric acid (935 mg, 1.0 eq) in ethanol. The salt crystallized out: 0.99 gm, 203°-205° C. A second crop of 0.73 in (m.p.=198°-200° C.) was collected later.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customwas removed
  4. customto leave a crude solid
  5. filtrationThe insolubles were filtered
  6. extractionthen extracted with DCM (2×250 ml)
  7. washThe DCM solution was washed with brine
  8. dry with materialdried over MgSO4
  9. customThe solvent was removed
  10. customto produce a colorless oil
  11. customThe salt crystallized out
  12. custom0.99 gm, 203°-205° C
  13. customA second crop of 0.73 in (m.p.=198°-200° C.) was collected later

Sources & evidence

ORD record
ord-7efea427658545c3a2e55a352ba75c29
Source dataset
uspto-grants-1994_11
Patent number
US05364866

Reaction notes

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