Hydrochloric Acid → 3-(Dimethylaminomethyl)-7-azaindole

HRID 530922Notes

Reaction equation

HRID 530922 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.Cl.[CH3:11][NH:12][CH3:13].[CH2:14]=O.Cl>C(OC)(C)(C)C.O.C(O)CCC>[CH3:11][N:12]([CH3:14])[CH2:13][C:3]1[C:4]2[C:9](=[N:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 53835493-(Dimethylaminomethyl)-7-azaindoleYield 80.5%

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 7-azaindole (150 g), dimethylamine hydrochloride (114 g) and 1-butanol (1.275 L) was added a 37% aqueous formaldehyde solution (103 g), and the mixture was stirred on a 120° C. oil bath for 2.5 hours. The reaction solution was cooled to around 40° C., and placed into water (1.35 L), concentrated hydrochloric acid (54 mL) and methyl tert-butyl ether (MTBE) (630 mL) were added, the mixture was stirred, the layers were separated, and the aqueous layer was taken. This aqueous layer was further washed with MTBE, and a 48% aqueous sodium hydroxide solution was added. This was extracted with chloroform, and a small amount of methanol was added to the extraction solution, followed by drying with anhydrous sodium sulfate. A desiccant was distilled off, followed by concentration under reduced pressure, to obtain the title compound (179 g) having the following physical property values.

Workup

  1. temperatureThe reaction solution was cooled to around 40° C.
  2. additionwere added
  3. stirringthe mixture was stirred
  4. customthe layers were separated
  5. washThis aqueous layer was further washed with MTBE
  6. additiona 48% aqueous sodium hydroxide solution was added
  7. extractionThis was extracted with chloroform
  8. additiona small amount of methanol was added to the extraction solution
  9. dry with materialby drying with anhydrous sodium sulfate
  10. distillationA desiccant was distilled off
  11. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-8fccccd32555449db4d502ba771a4b2c
Source dataset
uspto-grants-2016_05
Patent number
US09353113B2

Reaction notes

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