Hydrochloric Acid → Hydrochloric Acid

HRID 1397131Notes

Reaction equation

HRID 1397131 reaction equation
[ClH:1].C([O:9][CH2:10][C:11]([N:13]([CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[CH3:14])=[O:12])C1C=CC=CC=1.[H][H]>[Pd].CO>[CH3:18][N:17]([CH3:19])[CH2:16][CH2:15][N:13]([CH3:14])[C:11](=[O:12])[CH2:10][OH:9].[ClH:1]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 669739782-Benzyloxy-N-(2-(dimethylamino)ethyl)-N-methylacetamideHCID 178418361HCID 178418361, compound

Product 2

HCID 313Hydrochloric AcidHCID 54488530N-(2-(Dimethylamino)ethyl)-2-Hydroxy-N-methylacetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Crude HCl salt of 101 was mixed with 201.8 mg (0.1896 mmol) of palladium on charcoal (10%) in 15 mL of methanol. The mixture was subjected to hydrogen atmosphere at 50 psi on a Parr apparatus at room temperature. After overnight, another 200.9 mg of catalyst was needed. After overnight, reaction was completed and the insolubles was filtered off through glass fiber filter paper. The filtrate was concentrated to yield 254.6 mg (quant.) of product 102 as HCl salt: 1H NMR (400 MHz, CDCl3): δ 2.89 (s, 6H), 3.06 (s, 3H), 3.21 (t, J=6.6, 2H), 3.93 (t, J=6.6, 2H), 4.25 (s, 2H).

Workup

  1. waitAfter overnight
  2. customreaction
  3. filtrationthe insolubles was filtered off through glass fiber
  4. filtrationfilter paper
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-abe3ab045c924e32830dddca0b58c0d6
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

Loading…