HCID 86741181, compound → HCID 13300491, compound

HRID 979832Notes

Reaction equation

HRID 979832 reaction equation
[I-:1].[I-].[CH3:3][N:4]1[CH:32]=[CH:31][CH:30]=[C:6]([C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:29])[C:22]2[CH2:23][N:24]([CH3:28])[CH:25]=[CH:26][CH:27]=2)=[O:8])[CH2:5]1.[H][H]>C(O)C.O.[Pt]=O>[IH:1].[IH:1].[CH3:28][N:24]1[CH2:25][CH2:26][CH2:27][CH:22]([C:21]([NH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:7](=[O:8])[CH:6]2[CH2:30][CH2:31][CH2:32][N:4]([CH3:3])[CH2:5]2)=[O:29])[CH2:23]1

Participants

6

Reactant 2

HCID 86741181HCID 86741181, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13300491HCID 13300491, compound

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1,10-Bis[N-(1-methylnipecotoyl)amino]decane dihydriodide (Example 28) was prepared in accordance with the procedure described by Lasslo et al for related compounds (Lasslo, Marine and Waller, J. Org. Chem., Vol. 21, pages 958-960 (1956); Lasslo and Waller, J. Org. Chem., Vol. 22, pages 837-838 (1957)). Thus, 12.0 g (0.018 mole) of 1,10-bis[N-(1-methylnicotinoyl)amino]decane diiodide was dissolved in a mixture of 125 ml of absolute ethanol and 125 ml of water, and subjected to hydrogenation (at maximum pressures of 45-50 psi and at ambient temperature) in the presence of 1.0 g of platinum oxide (Adams' catalyst). When hydrogen uptake ceased, the catalyst was removed by filtration and the solvent by distillation under reduced pressure. Subsequent to drying at 75° C./0.020 mm Hg for 2 hr, the residue constituted the analytical sample (11.8 g, 96.7%) with the properties described in Table 1. In other instances, the products so obtained were purified by recrystallization from appropriate solvents.

Workup

  1. customthe catalyst was removed by filtration
  2. distillationthe solvent by distillation under reduced pressure
  3. customSubsequent to drying at 75° C./0.020 mm Hg for 2 hr
  4. customIn other instances, the products so obtained
  5. customwere purified by recrystallization from appropriate solvents

Sources & evidence

ORD record
ord-57a8535df7f545888809732c34de60ab
Source dataset
uspto-grants-1987_01
Patent number
US04634709

Reaction notes

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