Acetaldehyde, 2,2-dimethoxy- → 3,4-Dihydro-6-(2,2-dimethoxyethyl)amino-4-(2-dimethylaminoethyl)-2H-1,4-benzoxazine

HRID 1740746Notes

Reaction equation

HRID 1740746 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])[C:6]=2[CH:16]=1.[CH3:17][O:18][CH:19]([O:22][CH3:23])[CH:20]=O>[Pd].C(O)C>[CH3:17][O:18][CH:19]([O:22][CH3:23])[CH2:20][NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([CH2:11][CH2:12][N:13]([CH3:14])[CH3:15])[C:6]=2[CH:16]=1

Participants

5

Reactant 2

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 106805166-Amino-3,4-dihydro-4-(2-dimethylaminoethyl)-2H-1,4-benzoxazine

Product 1

HCID 218330383,4-Dihydro-6-(2,2-dimethoxyethyl)amino-4-(2-dimethylaminoethyl)-2H-1,4-benzoxazineYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-Amino-3,4-dihydro-4-(2-dimethylaminoethyl)-2H-1,4-benzoxazine (D3, 1.78 g, 8.1 mmol) and dimethoxyacetaldehyde (40% in MTBE, 3.1 g) were hydrogenated over 10% palladium on carbon (0.5g) in ethanol (70 ml) for 24 h. The catalyst was filtered off, and the filtrate was evaporated to dryness. The residue was dissolved in ethyl acetate, washed with water and brine, dried (Na2SO4) and evaporated to give the title compound (1.92 g, 77%) as a brown oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-416c6c1fa3614fd2bd21670ad55b2a8c
Source dataset
uspto-grants-1999_10
Patent number
US05972935

Reaction notes

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