Water → HCID 10165395, compound

HRID 279084Notes

Reaction equation

HRID 279084 reaction equation
[OH:1][C:2]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH2:33][CH2:34][O:35]C(=O)C)[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([OH:13])=O)[CH2:4][CH2:3]1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:51]([NH2:55])[CH2:52][CH2:53][CH3:54].O>CN(C)C=O>[OH:1][C:2]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH2:33][CH2:34][OH:35])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:11]([NH:55][CH2:51][CH2:52][CH2:53][CH3:54])=[O:13])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8007ButylamineHCID 682631,1'-CarbonyldiimidazoleHCID 15540985HCID 15540985, compound

Product 1

HCID 10165395HCID 10165395, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 5 mL of anhydrous dimethylformamide was dissolved 81 mg (0.17 mmol) of 4-(4-hydroxy-4-(2-(2-acetoxyethoxy)phenyl)piperidino)-2,2-diphenylbutyric acid. The resulting solution was stirred at room temperature for 1 hour. To the reaction mixture were added 36 mg (0.22 mmol) of carbodiimidazole, and after one hour 16 mg (0.22 mmol) of n-butylamine. After stirring at 70° C. for 24 hours, stirring was conducted for further 3 hours at 130° C., whereby the reaction was completed. Water was added to the reaction mixture, followed by extraction with ethyl acetate, washing with water and drying. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on an alumina column and then chromatography on a silica gel column, whereby 35 mg (yield: 38.9%) of 4-(4-hydroxy-4-(2-(2-hydroxyethoxy)phenyl)piperidino)-N-butyl-2,2-diphenylbutaneamide (Compound No. 73) was obtained.

Workup

  1. stirringAfter stirring at 70° C. for 24 hours
  2. stirringstirring
  3. waitwas conducted for further 3 hours at 130° C.
  4. extractionfollowed by extraction with ethyl acetate
  5. washwashing with water
  6. customdrying
  7. customThe residue obtained
  8. distillationby distilling off the solvent under reduced pressure
  9. customwas purified by chromatography on an alumina column

Sources & evidence

ORD record
ord-f0221102e7db4164a23a53ac3b0fab64
Source dataset
uspto-grants-2002_03
Patent number
US06362203B1

Reaction notes

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