Potassium Carbonate → HCID 22099464, compound

HRID 1457605Notes

Reaction equation

HRID 1457605 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13]I)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)P(N(C)C)(N(C)C)=O>O>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][N:25]1[CH2:26][CH2:27][N:22]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:23][CH2:24]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 759941-BenzylpiperazineHCID 11301181Benzyl (2-iodoethyl)carbamate

Product 1

HCID 22099464HCID 22099464, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.92 g of N-benzyloxycarbonyl-2-iodo-ethylamine, 4.00 g of 1-benzylpiperazine, 15.66 g of potassium carbonate and 40 ml of hexamethylphosphoramide (HMPA) was stirred at room temperature for overnight. Water was added to the reaction mixture, and the resulting mixture was extracted with diethyl ether. The extract was washed and dried, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent; chloroform:methanol=15:1) to give 5.63 g of N-benzyloxycarbonyl-2-(4-benzylpiperazin-1-yl)ethylamine (yield: 70%, oily product, IR: 3230, 2910, 1710 cm-).

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe extract was washed
  3. customdried
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent; chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-8882b3d22c5349a2adaff0d47fe1a0e0
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

Loading…