HCID 584108, compound → HCID 12447264, compound

HRID 2387239Notes

Reaction equation

HRID 2387239 reaction equation
[CH3:1][C:2]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:6])[C:3]([NH2:5])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:6][C:2]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:1])[CH2:3][NH2:5]

Participants

4

Reactant 2

HCID 584108HCID 584108, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12447264HCID 12447264, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-Methyl-2-phenylamino-propionamide (1 eq) in dry THF (0.2 M) was added dropwise to a stirred ice-cooled suspension of LiAlH4(6 eq) in dry THF (1.2 M) under N2. Upon completion of the addition, the reaction mixture was refluxed for 24 h. The mixture was cooled to 0° C., quenched with water and filtered through Celite. The filtrate was concentrated under reduced pressure and partitioned between water and DCM. The organic phase was separated and washed with brine, then dried (Na2SO4) and concentrated under reduced pressure to yield KK1 as reddish oil which was used as such in the next step. MS (ES) C10H16N2 requires: 164, found: 165 (M+H)+.

Workup

  1. temperaturecooled
  2. additionUpon completion of the addition
  3. temperaturethe reaction mixture was refluxed for 24 h
  4. customquenched with water
  5. filtrationfiltered through Celite
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompartitioned between water and DCM
  8. customThe organic phase was separated
  9. washwashed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated under reduced pressure
  12. customto yield KK1 as reddish oil which

Sources & evidence

ORD record
ord-2f2cc239823f48a1a2f97cc7c3d8c18d
Source dataset
uspto-grants-2012_09
Patent number
US08268827B2

Reaction notes

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