2-Phenylglutaric anhydride → HCID 88678971, compound

HRID 280350Notes

Reaction equation

HRID 280350 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]2[N:15]([CH2:16][C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)[C:14]3[CH:22]=[CH:23][CH:24]=[CH:25][C:13]=3[N:12]=2)[CH2:6][CH2:5]1.C1(C2CCC(=O)[O:34][C:33]2=O)C=CC=CC=1>CN(C)C=O>[OH2:18].[O:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[CH2:16][N:15]1[C:14]2[CH:22]=[CH:23][CH:24]=[CH:25][C:13]=2[N:12]=[C:11]1[NH:10][CH:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:1][CH:33]=[O:34])[CH2:5][CH2:6]1.[O:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[CH2:16][N:15]1[C:14]2[CH:22]=[CH:23][CH:24]=[CH:25][C:13]=2[N:12]=[C:11]1[NH:10][CH:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:1][CH:33]=[O:34])[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 962932-Phenylglutaric anhydrideHCID 13588039N-[1-(2-aminoethyl)-4-piperidinyl]-1-(2-furanylmethyl)-1H-benzimidazol-2-amine

Product 1

HCID 88678971HCID 88678971, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 5.09 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-1-(2-furanylmethyl)-1H-benzimidazol-2-amine and 54 parts of N,N-dimethylformamide was stirred and heated at 50° C. and there was added dropwise a solution of 2.8 parts of dihydro-3-phenyl-2H-pyran-2,6(3H)dione in 18 parts of N,N-dimethylformamide. Upon completion, stirring was continued overnight at 50° C. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was from a mixture of acetonitrile and 2,2'-oxybispropane, yielding 1.8 parts of N-[2-[4-[[1-(2-furanylmethyl)-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]formamide hemihydrate; mp. 125.2° C. (compound 46).

Workup

  1. stirringUpon completion, stirring
  2. customThe residue was purified by column chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated
  6. additionThe residue was from a mixture of acetonitrile and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-860d3a453ea64aa4a5de0f27c839b1e0
Source dataset
uspto-grants-1986_05
Patent number
US04588722

Reaction notes

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