Water → HCID 18174654, compound

HRID 427709Notes

Reaction equation

HRID 427709 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH2:14])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25](O)=[O:26])([O-])=O.CCOC(C)=O.O>CN(C=O)C>[NH2:15][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25]([NH:14][CH2:13][CH:10]1[CH2:9][CH2:8][N:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:12][CH2:11]1)=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 77337(2-Nitrophenyl)acetic acidHCID 10607746[1-(Pyridin-4-yl)piperidin-4-yl]methanamine

Product 1

HCID 18174654HCID 18174654, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(4-pyridyl)piperidine-4-methylamine (156 mg, 0.817 mmol), 2-nitrophenylacetic acid (159 mg, 0.875 mmol) and 1-[3-(dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride (168 mg, 0.875 mmol) in DMF was stirred 16 h; and the mixture was poured into EtOAc and H2O. The aqueous layer was washed with EtOAc (2×) and the combined extracts were dried (K2CO3) and concentrated. The residue and 10% Pd/C (164 mg) in 25 mL of EtOH were placed under an atmosphere of hydrogen gas. After 2.5 h, the mixture was filtered and the filtrate concentrated. The residue was dissolved in 5% HOAc in MeOH and loaded onto a SCX Column (Varian). The column was eluted with MeOH followed by 2 M NH3 in MeOH. The latter fractions were concentrated yielding 158.6 mg (60%) of the title compound.

Workup

  1. washThe aqueous layer was washed with EtOAc (2×)
  2. dry with materialthe combined extracts were dried (K2CO3)
  3. concentrationconcentrated
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate concentrated
  6. dissolutionThe residue was dissolved in 5% HOAc in MeOH
  7. washThe column was eluted with MeOH
  8. concentrationThe latter fractions were concentrated

Sources & evidence

ORD record
ord-6bae5b526d44442f90a608061179d7e2
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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