Ethanol → HCID 67315568, compound

HRID 1012575Notes

Reaction equation

HRID 1012575 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][CH:21]=1)[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])(=[O:3])[CH3:2].C(O)C.[ClH:31].C(O)C.COCCOC>CC(O)C>[ClH:31].[C:1]([O:4][CH2:5][CH2:6][N:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][CH:21]=1)[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH2:14][CH3:15])[CH2:16][CH2:17][CH3:18])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 80711,2-DimethoxyethaneHCID 21887872Ethanol hydrochlorideHCID 67314829HCID 67314829, compound

Product 1

HCID 67315568HCID 67315568, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

6.95 g (0.0184 mol) of unpurified [(4-aminomethylbenzyl)-(4-dipropylaminobutyl)amino]ethyl acetate (14) synthesized in Example 16 and 50 ml of ethanol were charged in a 300 ml recovery flask. 9.8 g (0.066 mol, 3.6 equivalents) of a 25% hydrochloric acid-ethanol solution was added dropwise to the flask under cooling with ice, the mixture was warmed and stirred at room temperature for two hours. The reaction solution was then concentrated. After the addition of hexane to the residue, the mixture was reconcentrated, thereby obtaining foam-like slightly yellow crystals. After dissolving the crystals in 65 ml of IPA at 70° C., 50 ml of ethylene glycol dimethyl ether was added to the solution at 70° C. After stirring the mixture for one day, the precipitated white crystals were recovered by filtration. The crystals were then washed with ethylene glycol dimethyl ether and dried under reduced pressure, thereby obtaining 5.8 g of [(4-aminomethylbenzyl)-(4-dipropylaminobutyl)amino]ethyl acetate hydrochloride (14a) (yield: 64%). [HPLC: 99.0% (HPLC measurement conditions A)] m.p. 105 to 106° C.

Workup

  1. temperatureunder cooling with ice
  2. temperaturethe mixture was warmed
  3. concentrationThe reaction solution was then concentrated
  4. additionAfter the addition of hexane to the residue
  5. customobtaining foam-like slightly yellow crystals
  6. stirringAfter stirring the mixture for one day
  7. filtrationthe precipitated white crystals were recovered by filtration
  8. washThe crystals were then washed with ethylene glycol dimethyl ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-6cccd021a24a4f3da9bb00a3f3fa83db
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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