Toluene → N'-(tetrahydro-1H-pyrrolizin-7a(5H)-ylmethyl)-2-(2propyloxy)phenylurea

HRID 976443

Reaction equation

HRID 976443 reaction equation
[CH:1]([O:4][C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:19](Cl)(Cl)=[O:20].C1(C)C=CC=CC=1.[CH2:30]1[C:37]2([CH2:38][NH2:39])[N:33]([CH2:34][CH2:35][CH2:36]2)[CH2:32][CH2:31]1>C(Cl)(Cl)Cl>[CH2:30]1[C:37]2([CH2:38][NH:39][C:19](=[O:20])[NH:7][C:6]3[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=3[O:4][CH:1]([CH3:3])[CH3:2])[N:33]([CH2:34][CH2:35][CH2:36]2)[CH2:32][CH2:31]1

Participants

7

Reactant 5

HCID 1140TolueneHCID 6371PhosgeneHCID 8471TriethylamineHCID 344362-(1-Methylethoxy)benzenamineHCID 10654304(Hexahydro-1H-pyrrolizin-7A-YL)methanamine

Product 1

HCID 15224942N'-(tetrahydro-1H-pyrrolizin-7a(5H)-ylmethyl)-2-(2propyloxy)phenylureaYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-isopropoxy-aniline (123 mg, 0.813 mmole) was dissolved in CHCl3 (1 ml), added triethyl amine (0.113 ml, 0.813 mmole). Cooled soln. to 0° C., added a solution of phosgene in toluene (0.458 ml, 0.927 mmole) and stirred for 1.5 hours. To this solution was added tetrahydro-1H-pyrrolizin-7a(5H)-methylamine (114 mgs, 0.813 mmole) in CHCl3 and stirred for 18 hours. Solvent removed via rotary evaporator to give crude product as a solid. Solid was chromatographed on silica gel eluting with 5% CH3OH(NH3 ↑)/CHCl3 to give 220 mg (85%) of title compound as free base.

Workup

  1. temperatureCooled soln
  2. stirringstirred for 18 hours
  3. customSolvent removed via rotary evaporator
  4. customto give crude product as a solid
  5. customSolid was chromatographed on silica gel eluting with 5% CH3OH(NH3 ↑)/CHCl3

Sources & evidence

ORD record
ord-9055b495843d4c9e9af05f6695e4aa06
Source dataset
uspto-grants-1997_03
Patent number
US05612366

Linked notes

Loading…