Thionyl Chloride → HCID 69448829, compound

HRID 2060060Notes

Reaction equation

HRID 2060060 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][N:6]([CH2:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)O)[CH3:7]>>[ClH:3].[CH3:5][N:6]([CH3:7])[CH2:8][C:9]1[CH2:17][C:16]2[C:11]([C:10]=1[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)=[CH:12][CH:13]=[CH:14][CH:15]=2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 11543569HCID 11543569, compound

Product 1

HCID 69448829HCID 69448829, compound

Conditions

Temperature
65 °C

Procedure

2.6 ml of thionyl chloride were added dropwise, with the pronounced evolution of gas, to 2.17 g of 2-dimethylaminomethyl-1-pyridin-3-yl-indan-1-ol (mixture of the diastereoisomers), and the mixture was heated for 2.5 hours at 65° C., with stirring, and then concentrated in a water-jet pump. After cooling, first water and then 1 M sodium carbonate solution were added, and extraction was then carried out with tetrahydrofuran/ethyl acetate; the combined extracts were dried over magnesium sulfate, filtered and concentrated. The resulting crude product (1.4 g) was dissolved in about 17 ml of absolute ethanol and converted into the corresponding hydrochloride with water and chlorotrimethylsilane. The resulting solid was filtered off with suction, washed with a small amount of absolute ethanol and dried at 120° C. in vacuo (about 50 mbar). 1.74 g of dimethyl-(3-pyridin-3-yl-1H-inden-2-ylmethyl)-amine hydrochloride having a melting point of from 156° C. to 159° C. were obtained.

Workup

  1. additionmixture of the diastereoisomers), and the mixture
  2. concentrationconcentrated in a water-jet pump
  3. temperatureAfter cooling
  4. additionfirst water and then 1 M sodium carbonate solution were added
  5. extractionextraction
  6. dry with materialthe combined extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dissolutionThe resulting crude product (1.4 g) was dissolved in about 17 ml of absolute ethanol
  10. filtrationThe resulting solid was filtered off with suction
  11. washwashed with a small amount of absolute ethanol
  12. customdried at 120° C. in vacuo (about 50 mbar)

Sources & evidence

ORD record
ord-3907196f71d048ca8d7597a7d489beb5
Source dataset
uspto-grants-2012_10
Patent number
US08278338B2

Reaction notes

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