Dimethylamine → N,N,1-Trimethyl-1,3,4,9-Tetrahydropyrano[3,4-b]Indole-1-Acetamide

HRID 1833599Notes

Reaction equation

HRID 1833599 reaction equation
[CH3:1][C:2]1([CH2:15][C:16]([OH:18])=O)[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.[CH2:19]([N:21](CC)[CH2:22]C)C.ClC(OCC)=O.CNC>O1CCCC1>[CH3:19][N:21]([CH3:22])[C:16](=[O:18])[CH2:15][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

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 104905711-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid

Product 1

HCID 12204534N,N,1-Trimethyl-1,3,4,9-Tetrahydropyrano[3,4-b]Indole-1-Acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

To a stirred solution of 1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid (15 g, 0.061 mole), prepared as described in Example 1, in dry tetrahydrofuran (300 ml), cooled to -5° C., is added triethylamine (18.5 g, 0.183 mole), followed by ethyl chloroformate (16.6 g, 0.153 mole). The mixture is stirred at -5° C. for 2 hr. This mixture, which now contains the mixed anhydride of the above starting material, is added dropwise to a cooled 40% aqueous solution of the amine, dimethylamine (225 ml). The resulting mixture is stirred at room temperature for one-half hour. Most of the tetrahydrofuran is evaporated, and the residue partitioned between chloroform and water. The organic phase is washed with water, dried over sodium sulfate, and evaporated under reduced pressure. The residue is subjected to chromatography on silica gel. Elution with 20% ethyl acetate in benzene, followed by crystallization of the elute from ethyl acetate affords the title compound, m.p. 149° - 151° C., νmaxCHCl3 3375, 1634 cm-1.

Workup

  1. stirringThe resulting mixture is stirred at room temperature for one-half hour
  2. customMost of the tetrahydrofuran is evaporated
  3. customthe residue partitioned between chloroform and water
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. washElution with 20% ethyl acetate in benzene
  8. customfollowed by crystallization of the
  9. washelute from ethyl acetate

Sources & evidence

ORD record
ord-3f6147f9896948ecadf39a61d4895ebb
Source dataset
uspto-grants-1978_01
Patent number
US04066779

Reaction notes

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