Hydrochloric Acid → HCID 67315290, compound

HRID 1012586Notes

Reaction equation

HRID 1012586 reaction equation
[C:1]([O:4][CH:5]([N:12]([CH2:33][CH2:34][CH2:35][CH2:36][N:37]([CH2:41][CH2:42][CH3:43])[CH2:38][CH2:39][CH3:40])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]=CC2C=CC(C(F)(F)F)=CC=2)=[CH:16][CH:15]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2].Cl>C(O)C>[C:1]([O:4][CH:5]([N:12]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH2:21])=[CH:16][CH:15]=1)[CH2:33][CH2:34][CH2:35][CH2:36][N:37]([CH2:38][CH2:39][CH3:40])[CH2:41][CH2:42][CH3:43])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67315271HCID 67315271, compound

Product 1

HCID 67315290HCID 67315290, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

In a 50 ml recovery flask, 517 mg (0.87 mmol, 1.0 equivalent) of {(4-dipropylaminobutyl)-[4-(4-trifluoromethylbenzylidene)aminomethylbenzyl]}amino}benzyl acetate (32) was dissolved in 5.2 ml of ethanol. The solution was cooled to 0° C. After the dropwise addition of 5.2 ml of 2N hydrochloric acid over about five minutes, the mixture was reacted at 0° C. for 5.6 hours. The reaction solution was extracted five times with 25 ml of chloroform. The aqueous layer was slowly added with 50 ml of chloroform and 40 ml of a 3N sodium hydroxide aqueous solution to make the mixture basic. The mixture was subjected to phase separation, and then extracted three times with 25 ml of chloroform. The extract was dried over anhydrous sodium sulfate, filtered, and concentrated, thereby obtaining 272.9 mg of [(4-aminomethylbenzyl)-(4-dipropylaminobutyl)amino]benzyl acetate (39) as a slightly yellow oily substance (yield: 72%). [HPLC: 97% (HPLC measurement conditions B)]

Workup

  1. customthe mixture was reacted at 0° C. for 5.6 hours
  2. extractionThe reaction solution was extracted five times with 25 ml of chloroform
  3. additionThe aqueous layer was slowly added with 50 ml of chloroform and 40 ml of a 3N sodium hydroxide aqueous solution
  4. customThe mixture was subjected to phase separation
  5. extractionextracted three times with 25 ml of chloroform
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8219712a49014cceb73c2b9d52e1c9db
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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