Methylamine → HCID 12800950, compound

HRID 225133Notes

Reaction equation

HRID 225133 reaction equation
[CH3:1][C:2]1([CH:15]2[CH2:19][CH2:18][O:17][C:16]2=[O:20])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[CH3:21][NH2:22]>O1CCCC1.[Cl-].[Na+].O>[CH3:21][NH:22][C:16](=[O:20])[CH:15]([CH2:19][CH2:18][OH:17])[C:2]1([CH3:1])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

5

Reactant 2

HCID 6329MethylamineHCID 12507637HCID 12507637, compound

Product 1

HCID 12800950HCID 12800950, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 4,5-dihydro-3-(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indole-1-yl)-2(3H)-furanone (described in Example 1, 20 g, 0.074 mole) in tetrahydrofuran (200 ml) and 40% aqueous methylamine-(200 ml)-is refluxed for 24 hr. The reaction mixture is diluted with brine and extracted with diethyl ether. The organic extracts are washed with brine, dried over magnesium sulfate and evaporated. The residue is subjected to chromatography on silica gel using acetone-benzene (1:2). The eluates are evaporated and crystallized from diethyl ether-hexane to obtain isomer A (6.9 g) of the title compound, mp 169°-171° C. The eluant for the column is changed to acetone-benzene (1:1) and the eluates are evaporated followed by trituration of the residue to obtain isomer B (7.5 g) of the title compound, mp 194°-196° C.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic extracts are washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe eluates are evaporated
  6. customcrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-24a2fccefe494972979cd12379fa449f
Source dataset
uspto-grants-1980_11
Patent number
US04235901

Reaction notes

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