Dimethylformamide → HCID 22099417, compound

HRID 1457608Notes

Reaction equation

HRID 1457608 reaction equation
CN(C)C=O.[H-].[Na+].C(OC(N[NH:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)=O)C1C=CC=CC=1.[CH2:29]([N:33]([CH2:38][CH2:39][CH2:40]Cl)[CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH3:32].[C:42]([O:45][CH2:46][CH3:47])(=[O:44])C>C(O)C.C(Cl)(Cl)Cl.CCCCCC.O>[CH2:46]([O:45][C:42]([NH:19][CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:40][CH2:39][CH2:38][N:33]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:29][CH2:30][CH2:31][CH3:32])=[CH:26][CH:27]=1)=[O:44])[C:47]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

10

Reactant 5

HCID 6228Dimethylformamide2×HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 96084N-(3-Chloropropyl)dibutylamineHCID 22099478HCID 22099478, compound

Product 1

HCID 22099417HCID 22099417, compoundYield 63%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 8058HexaneSolvent

Procedure

Under ice-cooling, to 20 ml of a dimethylformamide (DMF) suspension containing 850 mg of 62% sodium hydride was added little by little 5.4 g of N-benzyloxycarbonylamino-2-(4-hydroxyphenyl)ethylamine, and the mixture was stirred at room temperature for 20 minutes. Then, the mixture was ice-cooled, 10 ml of a DMF solution containing 4.5 g of N,N-dibutyl-3-chloropropylamine was added thereto. Further, after stirring the mixture at room temperature for 24 hours, water was added thereto and the mixture was extracted with diethyl ether. The extract was washed and dried, and the solvent was removed from the extract under reduced pressure. The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1 and then chloroform:ethanol=20:1) to give 5.5 g of N-benzyloxycarbonyl-2-[4-(3-dibutylaminopropyloxy)phenyl]ethylamine (yield: 63%, oily product, IR (film): 3310, 1710 cm-1).

Workup

  1. temperaturecooled
  2. additionwas added
  3. stirringFurther, after stirring the mixture at room temperature for 24 hours
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe extract was washed
  6. customdried
  7. customthe solvent was removed from the
  8. extractionextract under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (solvent

Sources & evidence

ORD record
ord-0541026f42ff463a91ea16d910d4cd70
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

Loading…