Aminoacetaldehyde dimethyl acetal → HCID 178495871, compound

HRID 575038Notes

Reaction equation

HRID 575038 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]2[C:5]([CH:6]3[CH2:14][CH:8]([N:9]=[C:10]2Cl)[CH2:7]3)=[CH:4][CH:3]=1.[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][NH2:19]>CC(O)(C)C>[Br:1][C:2]1[CH:12]=[C:11]2[C:5]([CH:6]3[CH2:14][CH:8]([N:9]=[C:10]2[NH:19][CH2:18][CH:17]([O:20][CH3:21])[O:16][CH3:15])[CH2:7]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 86693068HCID 86693068, compound

Product 1

HCID 178495871HCID 178495871, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
85 °C

Procedure

Into a 10-L 4-necked round-bottom flask was placed 5-bromo-8-chloro-9-azatricyclo[8.1.1.0[2,7]]dodeca-2,4,6,8-tetraene (260 g, 960.99 mmol, 1.00 equiv), 2-methylpropan-2-ol (6000 mL), and 2,2-dimethoxyethan-1-amine (600 g, 5.71 mol, 6.00 equiv). The resulting solution was stirred at 85° C. for 5 h, cooled to room temperature and concentrated under vacuum. The residue was washed with 2×500 mL water and extracted with 3×500 mL of ethyl acetate. The organic layers were combined and concentrated under vacuum to afford 340 g (crude) of 5-bromo-N-(2,2-dimethoxyethyl)-9-azatricyclo[8.1.1.0[2,7]]dodeca-2,4,6,8-tetraen-8-amine as a black oil.

Workup

  1. customInto a 10-L 4-necked round-bottom flask was placed
  2. temperaturecooled to room temperature
  3. concentrationconcentrated under vacuum
  4. washThe residue was washed with 2×500 mL water
  5. extractionextracted with 3×500 mL of ethyl acetate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-493e720583f24483842390ae70d3fe5b
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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