HCID 59857257, compound → HCID 45088570, compound

HRID 2377857Notes

Reaction equation

HRID 2377857 reaction equation
[CH3:1][N:2]([CH2:4][C@@H:5]1[O:10][CH2:9][C@@H:8]([CH3:11])[N:7](CC2C=CC=CC=2)[CH2:6]1)[CH3:3]>CCO.[Pd]>[CH3:3][N:2]([CH2:4][C@H:5]1[O:10][CH2:9][C@@H:8]([CH3:11])[NH:7][CH2:6]1)[CH3:1]

Participants

4

Reactant 1

HCID 59857257HCID 59857257, compound

Product 1

HCID 45088570HCID 45088570, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

(2S,5R)-2-[Dimethylamino(methyl)]-5-methyl-4-benzylmorpholine (28 g, 113 mmol, 1 equivalent), was dissolved in EtOH (1 M), and the solution was transferred to a stainless steel high pressure vessel equipped with a pressure gauge. 10% Pd/C was added (2.8 g, 10 wt. %), and the vessel charged with H2. The reaction mixture was stirred at 130° C. and 200 psi of H2 overnight. The reaction mixture was cooled to room temperature, filtered and evaporated. The desired amine was obtained in quantitative yield as a yellow oil. GC/MS: 128 (10%, M+−2×CH3), 58 (100%, NHCH2CHO), Rt 8.16 minutes.

Workup

  1. customthe solution was transferred to a stainless steel high pressure vessel
  2. customequipped with a pressure gauge
  3. additionthe vessel charged with H2
  4. custom200 psi of H2 overnight
  5. temperatureThe reaction mixture was cooled to room temperature
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-6cdde71519b04a65b632fb45225b3b94
Source dataset
uspto-grants-2008_12
Patent number
US07470709B2

Reaction notes

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