Dimethylamine → HCID 9889278, compound

HRID 413798Notes

Reaction equation

HRID 413798 reaction equation
[CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[CH:6]=[C:7]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:8][N:9]1[C:17]2[C:12](=[C:13]([O:18][CH2:19][CH:20]3[O:22][CH2:21]3)[CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:23]([O:25]C)=[O:24]>CO.CN(C=O)C>[Cl:4][C:5]1[CH:6]=[C:7]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:8][N:9]1[C:17]2[C:12](=[C:13]([O:18][CH2:19][CH:20]([OH:22])[CH2:21][N:2]([CH3:3])[CH3:1])[CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:23]([OH:25])=[O:24]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 18522120HCID 18522120, compound

Product 1

HCID 9889278HCID 9889278, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Dimethylamine in methanol (2.0 M, 2.14 ml) was added to a stirred solution of methyl N-(3,4-dichlorobenzyl)-4-(2,3-epoxypropyloxy)indole-2-carboxylate (87 mg) in DMF (5 ml) under an atmosphere of argon. The reaction was heated at 80° C. for 16 hours. The reaction was concentrated in vacuo and the residue partitioned between ethyl acetate and water. Combined organic extracts were washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated in vacuo. The residue was dissolved in THF (3 ml) and methanol (1.5 ml) and NaOH (2M, 3 ml) added and the reaction stirred for 16 hours. The reaction was then concentrated in vacuo and the residue dissolved in water. The solution was acidified by dropwise addition of acetic acid, resulting in the precipitation of a white solid which was filtered, washed with water and dried in vacuo to give the desired end product as a white solid (50 mg, 54%, 2 steps); NMR d (CD3SOCD3) 2.85 (s, 6H), 3.22-3.40 (m, 2H), 4.01-4.14 (m, 1H), 5.81 (s, 2H), 6.01 (d, 1H), 6.60 (d, 1H), 6.88 (dd, 1H), 7.13 (d, 1H), 7.21 (t, 1H), 7.28 (d, 1H), 7.44 (s, 1H), 7.53 (d, 1H); M/z (−) 435 (M−H+).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. washCombined organic extracts were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in THF (3 ml)
  7. additionmethanol (1.5 ml) and NaOH (2M, 3 ml) added
  8. concentrationThe reaction was then concentrated in vacuo
  9. dissolutionthe residue dissolved in water
  10. additionThe solution was acidified by dropwise addition of acetic acid
  11. customresulting in the precipitation of a white solid which
  12. filtrationwas filtered
  13. washwashed with water
  14. customdried in vacuo

Sources & evidence

ORD record
ord-6787a6e8e659497fa56c6e7166b77007
Source dataset
uspto-grants-2003_05
Patent number
US06569888B1

Reaction notes

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