1,1'-Carbonyldiimidazole → (+/-)-1-[3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl)amino]propyl]-tetrahydro-2(1H)-pyrimidinone

HRID 367281Notes

Reaction equation

HRID 367281 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=[CH:9]1)([N:3]1[CH:7]=[CH:6]N=C1)=[O:2].NCCCNCC[CH2:20][N:21]([CH2:29][CH:30]1[CH2:35][CH2:34][C:33]2[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=2[O:31]1)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[O:31]1[C:32]2[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=2[CH2:34][CH2:35][CH:30]1[CH2:29][N:21]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:20][CH2:11][CH2:12][N:8]1[CH2:9][CH2:6][CH2:7][NH:3][C:1]1=[O:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 22573235(+/-)-N-(3-aminopropyl)-N'-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-N'-(phenylmethyl)-1,3-propanediamine

Product 1

HCID 9930480(+/-)-1-[3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl)amino]propyl]-tetrahydro-2(1H)-pyrimidinoneYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1'-Carbonylbis-1H-imidazole (0.02 mol) was added to a solution of (±)-N-(3-aminopropyl)-N'-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-N'-(phenylmethyl)-1,3-propanediamine (0.02 mol) in THF (100 ml). The reaction solution was stirred for 17 hours at room temperature. The solvent was evaporated. Water was added to the residue and the mixture was extracted with toluene. The organic layer was separated, dried, filtered and the solvent evaporated. The residue was crystallized from ethyl acetate (50 ml). The precipitate was filtered off and dried, yielding 3.3 g (42%) of (±)-1-[3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl](phenylmethyl)amino]propyl]tetrahydro-2(1H)-pyrimidinone (comp. 13); mp. 94.7° C.

Workup

  1. customThe solvent was evaporated
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with toluene
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was crystallized from ethyl acetate (50 ml)
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-09bfe8d3e6fa4aca85281e4b51f68e80
Source dataset
uspto-grants-2000_10
Patent number
US06133277

Reaction notes

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