1,2-Dichloroethane → Phenylmethyl 4-[(4-pyridinylamino)carbonyl]-1-piperidinecarboxylate

HRID 1827113Notes

Reaction equation

HRID 1827113 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[N:24]1[CH:25]=[CH:26][C:21]([NH:20][C:17]([CH:14]2[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:16][CH2:15]2)=[O:19])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 17274-AminopyridineHCID 181649HOAtHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Product 1

HCID 13937700Phenylmethyl 4-[(4-pyridinylamino)carbonyl]-1-piperidinecarboxylateYield 89.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (5 mL), 1-[(benzyloxy)carbonyl]-4-piperidinecarboxylic acid (P. E. Maligres et al., Tetrahedron, 53:10983 (1997)) (1.00 g, 3.80 mmol), 4-aminopyridine (572 mg, 6.08 mmol), EDC (801 mg, 4.18 mmol), and HOAt (569 mg, 4.18 mmol) were combined and aged under N2 for 4 h. The reaction was partitioned between sat. NaHCO3 and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×). The combined organics were washed with water and brine then dried over Na2SO4, filtered and concentrated under reduced pressure, affording 1.16 g of benzyl 4-[(4-pyridinylamino)carbonyl]-1-piperidinecarboxylate as a yellow oil which was used without further purification.

Workup

  1. customThe reaction was partitioned between sat. NaHCO3 and ethyl acetate
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×)
  4. washThe combined organics were washed with water and brine
  5. dry with materialthen dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84c1085325034a38b36001d97a748395
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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