HCID 14116886, compound → HCID 14372569, compound

HRID 1382974Notes

Reaction equation

HRID 1382974 reaction equation
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([O:19][CH2:20][C:21]#[N:22])[CH:3]=1>[Ni]>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[O:7])=[C:4]([O:19][CH2:20][CH2:21][NH2:22])[CH:3]=1

Participants

3

Reactant 1

HCID 14116886HCID 14116886, compound

Product 1

HCID 14372569HCID 14372569, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a suspension of one teaspoonful of Raney nickel (well washed with methanol) in methanol (130 ml) was added 4-amino-5-chloro-2-cyanomethyl-N-[2-(diethylamino)ethyl]benzamide (12.05 g, 37.1 mmoles) (prepared in Example 13), and the mixture hydrogenated at 40 psi for 5 hours. The catalyst was removed by filtration under nitrogen and the filtrate concentrated in vacuo. This was dissolved in methylene chloride and washed with 1N sodium hydroxide (4×25 ml). The washings were back extracted with methylene chloride and the organic phases combined, dried and concentrated in vacuo to give 5.56 g of the title product as a semi-solid. This was recrystallized from methanol-ether in the cold to give a sample, mp. 97°-99° C.

Workup

  1. washwell washed with methanol) in methanol (130 ml)
  2. customThe catalyst was removed by filtration under nitrogen
  3. concentrationthe filtrate concentrated in vacuo
  4. dissolutionThis was dissolved in methylene chloride
  5. washwashed with 1N sodium hydroxide (4×25 ml)
  6. extractionThe washings were back extracted with methylene chloride
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a53061b78a69481f80083b1c082c4493
Source dataset
uspto-grants-1989_02
Patent number
US04808624

Reaction notes

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