1,1'-Carbonyldiimidazole → HCID 14327083, compound

HRID 650283Notes

Reaction equation

HRID 650283 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:25][NH:26][CH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH:28]1[N:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:26]([CH:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:29][CH:28]2[N:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)[CH3:25])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 798743,4-Dichlorophenylacetic acidHCID 14126788HCID 14126788, compound

Product 1

HCID 14327083HCID 14327083, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 2.66 g of 3,4-dichlorophenylacetic acid, 2.11 g of carbonyldiimidazole and 20 ml of tetrahydrofuran was stirred for 1 hour and then a solution of 2.16 g of the product of Step B in 5 ml of tetrahydrofuran was added slowly. The mixture was stirred for 3 hours 30 minutes and then the tetrahydrofuran was distilled off under reduced pressure. The residue was taken up in 100 ml of ether and after washing with a saturated solution of sodium bicarbonate, then with saturated salt water, drying and concentrating to dryness under reduced pressure, 4.68 g of [Trans (±)] 3,4-dichloro-N-[2,3-dihydro-2-(1-pyrrolidinyl)-1H-inden-1-yl]-N-methyl-benzene-acetamide in the form of a base were obtained.

Workup

  1. stirringThe mixture was stirred for 3 hours 30 minutes
  2. distillationthe tetrahydrofuran was distilled off under reduced pressure
  3. washafter washing with a saturated solution of sodium bicarbonate
  4. dry with materialwith saturated salt water, drying
  5. concentrationconcentrating to dryness under reduced pressure, 4.68 g of [Trans (±)] 3,4-dichloro-N-[2,3-dihydro-2-(1-pyrrolidinyl)-1H-inden-1-yl]-N-methyl-benzene-acetamide in the form of a base
  6. customwere obtained

Sources & evidence

ORD record
ord-55afeab838f447d0b2fb9cba03cc843c
Source dataset
uspto-grants-2001_08
Patent number
US06271395B1

Reaction notes

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