1,1'-Carbonyldiimidazole → HCID 59856527, compound

HRID 469351Notes

Reaction equation

HRID 469351 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[F:13][C:14]1[C:15]([N+:24]([O-:26])=[O:25])=[C:16]([CH2:20][C:21]([OH:23])=O)[CH:17]=[CH:18][CH:19]=1.[NH2:27][CH:28]1[CH2:33][CH2:32][N:31]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:30][CH2:29]1>C1COCC1.CCOC(C)=O>[CH2:34]([N:31]1[CH2:32][CH2:33][CH:28]([NH:27][C:21](=[O:23])[CH2:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([F:13])[C:15]=2[N+:24]([O-:26])=[O:25])[CH2:29][CH2:30]1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 4158521-Benzyl-4-piperidylamineHCID 24824213(3-Fluoro-2-nitrophenyl)acetic acid

Product 1

HCID 59856527HCID 59856527, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

17.0 g (102 mmol) CDI were added at RT to 18.3 g (91.9 mmol) (3-fluoro-2-nitro-phenyl)-acetic acid in 500 mL THF and stirred for 30 min. Then 20.0 mL (95.8 mmol) 4-amino-1-benzylpiperidine were added and the mixture was stirred for a further 2 h. The reaction mixture was diluted with EtOAc and the organic phase was washed with water and saturated sodium chloride solution. The organic phase was dried on magnesium sulphate, filtered and evaporated down i. vac. The residue was triturated with DIPE and suction filtered.

Workup

  1. stirringthe mixture was stirred for a further 2 h
  2. washthe organic phase was washed with water and saturated sodium chloride solution
  3. customThe organic phase was dried on magnesium sulphate
  4. filtrationfiltered
  5. customevaporated down i
  6. customThe residue was triturated with DIPE and suction
  7. filtrationfiltered

Sources & evidence

ORD record
ord-d82c3ddb7fd445a28705712fd5bf24e4
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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