Ammonia → HCID 14986710, compound

HRID 1494153Notes

Reaction equation

HRID 1494153 reaction equation
[C:1]([CH2:3][CH2:4][CH:5]([O:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:2].N.[H][H]>CO.[Ni]>[NH2:2][CH2:1][CH2:3][CH2:4][CH:5]([O:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 14986715HCID 14986715, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14986710HCID 14986710, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of crude ethyl 7-cyano-5-[3-pyridyloxy)-heptanoate (1.74 g) in 50 mL of methanol saturated with ammonia is subjected to hydrogenation for 5 hours at 3 atmospheres pressure of hydrogen using Raney Nickel (1.0 ml aqueous suspension) as the catalyst. The catalyst is filtered off and washed with methanol. The filtrate is evaporated and the residue filtered through a plug of silica gel using ether as eluent to remove remaining triphenylphosphine oxide. The compound is eluted from the silica gel using methanol:triethylamine (95:5). The solvent is evaporated to yield ethyl 8-amino-5-(3-pyridyloxy)-octanoate; 1H NMR (CDCl3): delta 8.28 (br,1H), 8.19 (br,1H), 4.39 (m,1H), 4.08 (q,2H).

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with methanol
  3. customThe filtrate is evaporated
  4. filtrationthe residue filtered through a plug of silica gel
  5. customto remove
  6. washThe compound is eluted from the silica gel
  7. customThe solvent is evaporated

Sources & evidence

ORD record
ord-7998e46f6c2043768d70bef49c097a0f
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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