Dimethylamine → HCID 12507638, compound

HRID 225132Notes

Reaction equation

HRID 225132 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][NH:22][CH3:23].[Cl-].[Na+]>O1CCCC1>[OH:17][CH2:18][CH2:19][CH:15]([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)[C:16]([N:22]([CH3:23])[CH3:21])=[O:20]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5234Sodium ChlorideHCID 12507637HCID 12507637, compound

Product 1

HCID 12507638HCID 12507638, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the oil containing the two diasteriomers of dihydro-3-(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)-2(3H)-furanone (described in Example 1, 15 g, 0.055 mole) in tetrahydrofuran (200 ml) and an aqueous solution of dimethylamine (40%, 200 ml) is refluxed for 24 hr. Aqueous sodium chloride solution is added and the solution is extracted with diethyl ether. The organic extract is dried and evaporated to afford an oil consisting of two diastereoisomeric amides of the title compound. The oil is subjected to chromatography on silica gel using acetone-benzene (1:3). The eluates are evaporated and crystallized from benzene-hexane to obtain isomer A of the title compound as crystals (4.5 g), mp 158°-160° C. Further elution of the column with acetone-benzene (1:1), evaporation of the eluates and crystallization of the residue from benzene-hexane gives isomer B of the title compound as crystals (1.5 g), mp 159°-162° C.

Workup

  1. extractionthe solution is extracted with diethyl ether
  2. extractionThe organic extract
  3. customis dried
  4. customevaporated
  5. customto afford an oil

Sources & evidence

ORD record
ord-533b9e3f77b943fa82fb22480973c546
Source dataset
uspto-grants-1980_11
Patent number
US04235901

Reaction notes

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