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Water → HCID 58792696, compound

HRID 1365089
Notes
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Reaction equation

HRID 1365089 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[O:19])[C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:4].C([O-])([O-])=O.[K+].[K+].O.[C:27]([O:30][CH2:31]C)(=[O:29])[CH3:28].C[N:34]([CH:36]=O)[CH3:35]>>[CH3:31][O:30][C:27](=[O:29])[C:28]1[CH:17]=[CH:9][CH:8]=[CH:7][C:36]=1[NH:34][CH:35]1[CH2:18][CH2:6][N:5]([CH2:2][C:3](=[O:4])[NH:5][C:6]2[CH:7]=[CH:8][C:9]3[C:10](=[O:19])[C:11]4[C:16]([C:17]=3[CH:18]=2)=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 114486452-Chloro-N-(9-oxo-9H-fluoren-3-yl)-acetamide

Product 1

HCID 58792696HCID 58792696, compoundYield 77%

Conditions

Temperature
10 °C

Procedure

A mixture of 2-(Piperidine-4-yl-amino)-methyl benzoate (1100 mg, 4.70 mmol), 2-Chloro-N-(9-oxo-9H-fluoren-3-yl)-acetamide (1358 mg, 5 mmol) and K2CO3 (1380 mg, 10 mmol) in DMF (40 mL) was stirred at 10° C. for 2 hours and then at room temperature overnight. The reaction mixture was added to 50 mL water and 100 mL ethyl acetate, the organic phase was decanted and washed with water (3×50 mL), dried over sodium sulfate and a 2.8 M hydrogen chloride solution in absolute ethanol (1.80 mL) was added, to precipitate the hydrochloride, which was filtered off and washed with ethyl acetate. 1840 mg of a white solid were obtained. Yield: 77%.

Workup

  1. customat room temperature
  2. customovernight
  3. customthe organic phase was decanted
  4. washwashed with water (3×50 mL)
  5. dry with materialdried over sodium sulfate
  6. additiona 2.8 M hydrogen chloride solution in absolute ethanol (1.80 mL) was added
  7. customto precipitate the hydrochloride, which
  8. filtrationwas filtered off
  9. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-de5906374a9d403e8d8892522d3b5894
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07888510B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes