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

HRID 1108982Notes

Reaction equation

HRID 1108982 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].[CH2:23]1[C:30]2([CH2:31][NH2:32])[N:26]([CH2:27][CH2:28][CH2:29]2)[CH2:25][CH2:24]1>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH2:23]1[C:30]2([CH2:31][NH:32][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:26]([CH2:27][CH2:28][CH2:29]2)[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 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 2

HCID 1140TolueneSolventHCID 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 20%. 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, .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. additionto 0° C., added a solution of 20%
  3. stirringstirred for 18 hours
  4. customSolvent removed via rotary evaporator
  5. customto give crude product as a solid
  6. customSolid was chromatographed on silica gel eluting with 5% CH3OH(NH3↑)/CHCl3

Sources & evidence

ORD record
ord-56c3550765594ae3b81dae3031fa206a
Source dataset
uspto-grants-1994_06
Patent number
US05318977

Reaction notes

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