Nitrogen → HCID 18467343, compound

HRID 1601317Notes

Reaction equation

HRID 1601317 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][C:16]([N:18]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH2:21][CH2:20][CH2:19]4)=O)[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].N#N.[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42]>C1COCC1.C(O)C>[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42].[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][N:18]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH2:21][CH2:20][CH2:19]4)[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 444972Fumaric AcidHCID 15285676HCID 15285676, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18467343HCID 18467343, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethanone (5.5 g, 14 mmol) in THF (50 ml) was charged with lithium aluminum hydride (17 ml, 17 mmol, 1 M in ether) dropwise under N2 at room temperature. The mixture was stirred for 8 hours at room temperature. At the end of this period the excess of hydride was quenched with ice chips and 3 ml of 20% NaOH. The mixture was diluted with EtOAc (150 ml) and stirred for 1 hour. The EtOAc was dried with MgSO4 and filtered. The solvent was removed to dryness. The residue was purified by flash chromatography over a silica gel column (SiO2, 55 g; eluted with 1-3% CH3OH: DCM). The product thus obtained weighed 1.83 g. This material was dissolved into hot ethanol and was treated with a solution of fumaric acid (700 mg) in ethanol. The crystals were collected and weighed 1.85 g, m.p. 192-193° C.

Workup

  1. customAt the end of this period the excess of hydride was quenched with ice chips and 3 ml of 20% NaOH
  2. additionThe mixture was diluted with EtOAc (150 ml)
  3. stirringstirred for 1 hour
  4. dry with materialThe EtOAc was dried with MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed to dryness
  7. customThe residue was purified by flash chromatography over a silica gel column (SiO2, 55 g; eluted with 1-3% CH3OH: DCM)
  8. customThe product thus obtained
  9. customThe crystals were collected

Sources & evidence

ORD record
ord-fde13555cc2848c7b20cd994fb2f1215
Source dataset
uspto-grants-1999_11
Patent number
US05977113

Reaction notes

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