Hydrochloric Acid → HCID 67314829, compound

HRID 1012574Notes

Reaction equation

HRID 1012574 reaction equation
Cl.[C:2]([O:5][CH2:6][CH2:7][N:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][N:28]=CC2C=CC=CC=2)=[CH:23][CH:22]=1)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])(=[O:4])[CH3:3]>C(O)C>[C:2]([O:5][CH2:6][CH2:7][N:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH2:28])=[CH:23][CH:22]=1)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:14][CH2:15][CH3:16])[CH2:17][CH2:18][CH3:19])(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67315886HCID 67315886, compound

Product 1

HCID 67314829HCID 67314829, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

362 ml of 2N hydrochloric acid was charged in a 2-liter four-necked flask and cooled to 0° C. The solution prepared by dissolving 32.8 g of {[4-(benzylidene)aminomethylbenzyl]-(4-dipropylaminobutyl)amino}ethyl acetate (8a) in 120 ml of ethanol was added dropwise to the flask for about 20 minutes, the mixture was stirred at room temperature for three hours. The resultant was extracted five times with 100 ml of toluene. After the addition of 400 ml of chloroform to the aqueous layer, 60 g of sodium carbonate was slowly added to the mixture while stirring to adjust to pH 9. The solution was subjected to phase separation and extracted again with 400 ml of chloroform. The chloroform layer was washed twice with 200 ml of a saturated sodium bicarbonate aqueous solution, washed twice with 200 ml of water, dried over anhydrous sodium sulfate, and concentrated, thereby obtaining 26.3 g of [(4-aminomethylbenzyl)-(4-dipropylaminobutyl)amino]ethyl acetate (14) (yield: 99%, GC: 95%).

Workup

  1. customThe solution prepared
  2. additionwas added dropwise to the flask for about 20 minutes
  3. extractionThe resultant was extracted five times with 100 ml of toluene
  4. additionAfter the addition of 400 ml of chloroform to the aqueous layer, 60 g of sodium carbonate
  5. additionwas slowly added to the mixture
  6. stirringwhile stirring
  7. customThe solution was subjected to phase separation
  8. extractionextracted again with 400 ml of chloroform
  9. washThe chloroform layer was washed twice with 200 ml of a saturated sodium bicarbonate aqueous solution
  10. washwashed twice with 200 ml of water
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-cf0ef15fab694ab98a74da998efaa2ae
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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