1,1'-Carbonyldiimidazole → HCID 70373894, compound

HRID 1650133Notes

Reaction equation

HRID 1650133 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N1C=CN=C1)(N1C=CN=C1)=[O:14].[N:25]1([CH2:30][CH:31]2[CH2:36][O:35][CH2:34][CH2:33][NH:32]2)[CH2:29][CH2:28][CH2:27][CH2:26]1>C(#N)C>[C:10]([OH:12])(=[O:11])/[CH:30]=[CH:31]\[C:36]([OH:35])=[O:14].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:32]2[CH2:33][CH2:34][O:35][CH2:36][CH:31]2[CH2:30][N:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 798743,4-Dichlorophenylacetic acidHCID 189150613-(Pyrrolidin-1-ylmethyl)morpholine

Product 1

HCID 70373894HCID 70373894, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 3,4-dichlorophenylacetic acid (410 mg) in acetonitrile (10 ml) was added a solution of 1,1'-carbonyldiimidazole (340 mg) in warm acetonitrile (10 ml). After 10 min a solution of the product of stage (iii) (330 mg) was added and the mixture was stirred at room temperature for 3.5 h. The solvent was removed in vacuo and the residue was partitioned between dichloromethane (40 ml) and 2N sodium carbonate (30 ml). The organic phase was separated and washed with water (20 ml). The dried organic layer was evaporated and the oily residue (0.77 g) was purified by column chromatography on alumina (Type UGI), eluting with ethyl acetate, to give the free base of the title compound as a gum (462 mg) a portion of which (452 mg) was treated with maleic acid (147 mg) and crystallised from ethyl acetate to give the title compound (365 mg), m.p. 129°-131°.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between dichloromethane (40 ml) and 2N sodium carbonate (30 ml)
  3. customThe organic phase was separated
  4. washwashed with water (20 ml)
  5. customThe dried organic layer was evaporated
  6. customthe oily residue (0.77 g) was purified by column chromatography on alumina (Type UGI)
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-0cdef29fefa04736821a3c224aa5cc20
Source dataset
uspto-grants-1990_05
Patent number
US04923863

Reaction notes

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