Hydrochloric Acid → (2-Methanesulfonylpyridin-4-yl)methanamine hydrochloride

HRID 559664Notes

Reaction equation

HRID 559664 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([CH2:11][NH:12]C(=O)OC(C)(C)C)[CH:8]=[CH:7][N:6]=1)(=[O:4])=[O:3].[ClH:20]>CC(O)C>[ClH:20].[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([CH2:11][NH2:12])[CH:8]=[CH:7][N:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59278429Tert-butyl (2-(methylsulfonyl)pyridin-4-yl)methylcarbamate

Product 1

HCID 53241148(2-Methanesulfonylpyridin-4-yl)methanamine hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

To a 500 mL reactor was charged tert-butyl (2-(methylsulfonyl)pyridin-4-yl)methylcarbamate (20.0 g, 65.65 mmol, 94.0 wt. %) followed by i-PrOH (140 mL). The slurry was stirred and treated with concentrated HCl (16.4 mL, 196.96 mmol, 3.0 eq), and then heated to 65° C. and held at this temperature for 3 hours. The batch was cooled to 20-25° C., held at this temperature for at least 2 hours, and then filtered. The solid was washed with i-PrOH and then oven dried under vacuum to afford the title compound as a white solid, 13.45 g, >99 wt. % purity, 92% yield.

Workup

  1. temperatureThe batch was cooled to 20-25° C.
  2. waitheld at this temperature for at least 2 hours
  3. filtrationfiltered
  4. washThe solid was washed with i-PrOH
  5. customoven dried under vacuum

Sources & evidence

ORD record
ord-0ad1b9bcd2cf4cc28e988feefaf64814
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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