Aminoacetaldehyde dimethyl acetal → HCID 69993910, compound

HRID 1936210Notes

Reaction equation

HRID 1936210 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[BrH:8].[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:5][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 110124391-[4-[(6-Bromohexyl)oxy]butyl]benzene

Product 1

HCID 69993910HCID 69993910, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 8.7 ml (79.85 mmol) aminoacetaldehyde dimethylacetal in 60 ml toluene at reflux is added dropwise a solution of 10 g (31.94 mmol) 4-(6-bromohexyloxy)butylbenzene in 40 ml toluene. After maintaining the reaction mixture under reflux for 4 hr, toluene is evaporated off under reduced pressure, and 50 ml CH2Cl2 is added thereto. The resulting solution is stirred for 15 min together with a solution of 20 ml 47% HBr diluted with 20 ml H2O. The reaction mixture is allowed to decant and the crude product obtained as a result of evaporating the CH2Cl2 phase to dryness is triturated with Et2O and filtered, thereby affording 4.31 g (32.3%) N-dimethoxyethyl-6-(4-phenylbutoxy)hexylamine hydrobromide.

Workup

  1. temperatureAfter maintaining the reaction mixture
  2. temperatureunder reflux for 4 hr
  3. customtoluene is evaporated off under reduced pressure, and 50 ml CH2Cl2
  4. additionis added
  5. additiondiluted with 20 ml H2O
  6. customto decant
  7. customthe crude product obtained as
  8. customa result
  9. customof evaporating the CH2Cl2 phase to dryness
  10. customis triturated with Et2O
  11. filtrationfiltered

Sources & evidence

ORD record
ord-621dfefb25d945e6ac6e25888e0824b6
Source dataset
uspto-grants-2002_05
Patent number
US06388134B1

Reaction notes

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