Dimethylamine → HCID 86752483, compound

HRID 1600176Notes

Reaction equation

HRID 1600176 reaction equation
[CH3:1][NH:2][CH3:3].[CH3:4][C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[CH:9][CH:8]=2.[CH2:26]=O.[OH-].[Na+]>C(O)(=O)C.O1CCCC1.C(OCC)(=O)C>[CH3:1][N:2]([CH2:26][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH:11]=2)[NH:6][C:5]=1[CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 86752484HCID 86752484, compound

Product 1

HCID 86752483HCID 86752483, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dimethylamine (3.35 ml of 33% solution in methylated spirit) was added to astirred mixture of benzyl (E)-3-(2-methyl-1H-indol-5-yl)-2-propenoate (6.50g) in a mixture of acetic acid (14 ml) and tetrahydrofuran (15 ml) at 0° C., followed by the dropwise addition of formaldehyde (1.75 ml of 40% aqueous solution). The mixture was stirred at room temperature for 3 hours and then diluted with ethyl acetate. 2N sodium hydroxide was addeddropwise with stirring until the pH of the aqueous layer was ca.9. The mixture was filtered, and the residue was washed with water followed by ethyl acetate and then dried to give the title compound (6.58 g), m.p. 174°-177° C. Found: C,75.85; H,6.83; N,7.53. C22 H24N2O2 requires: C,75.83; H,6.94; N,8.04%.

Workup

  1. stirringwith stirring until the pH of the aqueous layer
  2. filtrationThe mixture was filtered
  3. washthe residue was washed with water
  4. customdried

Sources & evidence

ORD record
ord-a286fb63155f4b669607a495368e1995
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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