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

HRID 2298800Notes

Reaction equation

HRID 2298800 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 (0.0(2 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-2e323ea0378d4122b54bea1236b5e084
Source dataset
uspto-grants-2002_12
Patent number
US06495547B1

Reaction notes

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