Hydrochloric Acid → (1,4-Dioxan-2-ylmethyl)methylamine hydrochloride

HRID 222273Notes

Reaction equation

HRID 222273 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH2:7][N:8](C)[C:9](=O)OCC1C=CC=CC=1.[ClH:20]>C(O)C.[Pd]>[ClH:20].[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH2:7][NH:8][CH3:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66972115Benzyl (1,4-dioxan-2-ylmethyl)methylcarbamate

Product 1

HCID 66972118(1,4-Dioxan-2-ylmethyl)methylamine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl (1,4-dioxan-2-ylmethyl)methylcarbamate (Enantiomer A, 2.9 g, 10.9 mmol) was dissolved in 50 mL dry ethanol. 10% (w/w) palladium on carbon (0.29 g) and 1.0 mL 10N HCl were added. The flask was sealed and flushed with hydrogen. Stirred solution under a hydrogen balloon. After 12 hours, the solution was filtered through celite and concentrated in vacuo to afford the title compound. 1H NMR (600 MHz, D6-DMSO) 8.64 (s, 2H); 3.82-3.75 (m, 2H); 3.69 (d, 1H); 3.64 (d, 1H); 3.59 (m, 1H); 3.44 (m, 1H); 3.22 (t, 1H); 2.94-2.84 (m, 2H); 2.51 (s, 3H).

Workup

  1. customThe flask was sealed
  2. customflushed with hydrogen
  3. filtrationthe solution was filtered through celite and
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1712bf8aa7f4dd9982ef5dbedcad567
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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