Nitrogen → HCID 18467343, compound

HRID 1955935Notes

Reaction equation

HRID 1955935 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-(6fluoro-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, 1M 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 rnl 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 rnl 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-8469ba4b06064ae0836f6244d55d292d
Source dataset
uspto-grants-1998_07
Patent number
US05776963

Reaction notes

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