Water → HCID 9864130, compound

HRID 478620Notes

Reaction equation

HRID 478620 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH:13][C:14](=[O:44])[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][N:24](C(OCC4C5C(=CC=CC=5)C5C4=CC=CC=5)=O)[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2].N1CCCCC1.O.C(OCC)(=O)C>CN(C=O)C>[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH:13][C:14](=[O:44])[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]3)=[CH:17][CH:16]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8082Piperidine2×HCID 8857Ethyl AcetateHCID 18002465HCID 18002465, compound

Product 1

HCID 9864130HCID 9864130, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[1-(Cyanomethyl-carbamoyl)-cyclohexyl]-4-(4-FMOC-piperazin-1-yl)-benzamide (4.4 mmol) is dissolved in DMF (15 ml), piperidine (4.4 mmol) is added and the mixture is stirred at RT for 4 hours. 4 additional drops of piperidine are added and the mixture is stirred over night. The reaction mixture is poured into water and ethyl acetate and the suspension is filtered and the filtrate is acidified with HCl 4N and then extracted with ethyl acetate. Saturated sodium carbonate solution is added to make the water phase basic and the mixture is extracted three times with ethyl acetate. The water phase is saturated with sodium chloride and extracted three times with ethyl acetate again. The organic fractions are dried over sodium sulfate and the solvent is evaporated. The residue is purified by flash chromatography on silica gel with CH2Cl2/MeOH (with 3N NH3)=95:5 as mobile phase. The product containing fractions are combined and evaporated. The residue is suspended in diethylether and the solid filtered of and dried (vacuum). A white powder with mp. 206-210° C., Rf=0.28 (CH2Cl2/MeOH (with 3N NH3)=9:1) is obtained.

Workup

  1. stirringthe mixture is stirred over night
  2. filtrationthe suspension is filtered
  3. extractionextracted with ethyl acetate
  4. additionSaturated sodium carbonate solution is added
  5. extractionthe mixture is extracted three times with ethyl acetate
  6. extractionextracted three times with ethyl acetate again
  7. dry with materialThe organic fractions are dried over sodium sulfate
  8. customthe solvent is evaporated
  9. customThe residue is purified by flash chromatography on silica gel with CH2Cl2/MeOH (with 3N NH3)=95:5 as mobile phase
  10. additionThe product containing fractions
  11. customevaporated
  12. filtrationthe solid filtered of and
  13. customdried (vacuum)
  14. customA white powder with mp. 206-210° C., Rf=0.28 (CH2Cl2/MeOH (with 3N NH3)=9:1) is obtained

Sources & evidence

ORD record
ord-a0252e5c89b840febb4d9d011c547ea0
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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