Hydrochloric Acid → Dibenzo[b,d]furan-2-ylmethanamine

HRID 594383Notes

Reaction equation

HRID 594383 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:14][NH:15]S(C(C)(C)C)=O.Cl.O1CCOCC1>CO>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:14][NH2:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86695631N-(dibenzo[b,d]furan-2-ylmethyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 64083279Dibenzo[b,d]furan-2-ylmethanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) solution of N-(dibenzo[b,d]furan-2-ylmethyl)-2-methylpropane-2-sulfinamide (2.280 g; 7.55 mmol) in MeOH (24 ml) was treated dropwise with a solution of 4 M HCl in 1,4-dioxane (4.0 ml; 16.00 mmol). The resulting mixture was further stirred at 0° C., under nitrogen, for 10 min., and then at rt for 1 h. The reaction mixture was concentrated to dryness under reduced pressure. DCM, water, and Na2CO3 (5.50 g) were added, and the organic layer was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording dibenzo[b,d]furan-2-ylmethanamine as a yellow solid. LC-MS (conditions A): tR=0.51 min.; no ionisation.

Workup

  1. waitat rt for 1 h
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  3. additionDCM, water, and Na2CO3 (5.50 g) were added
  4. dry with materialthe organic layer was then dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-097d3798033a45aab095d16366327653
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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