4-Methylmorpholine → HCID 67048415, compound

HRID 2094261Notes

Reaction equation

HRID 2094261 reaction equation
[C:1]([CH2:8][CH2:9][CH2:10][NH:11][NH2:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN1CCOCC1.[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1F)[C:24]#[N:25]>CN(C=O)C>[C:1]([CH2:8][CH2:9][CH2:10][N:11]([NH2:12])[C:28]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=1[Cl:20])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 1455253-Chloro-4-fluorobenzonitrileHCID 86600573HCID 86600573, compound

Product 1

HCID 67048415HCID 67048415, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.49 g (20 mmol) 3-Boc-amino-propylamine in 5 ml DMF are combined with 2.75 ml (25 mmol) NMM. After the addition of 3.11 g (20 mmol) 3-chloro-4-fluoro-benzonitrile the mixture is stirred for 3.5 hours at ambient temperature under a nitrogen atmosphere, heated to 105° C. for 20 minutes and extracted with ethyl acetate. The combined organic phases are washed with water and sat. sodium chloride solution, dried over magnesium sulphate and evaporated down i. vac. The residue is further reacted without any more purification.

Workup

  1. temperatureheated to 105° C. for 20 minutes
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases are washed with water and sat. sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated down i
  6. customThe residue is further reacted without any more purification

Sources & evidence

ORD record
ord-e647ccb3b2344de0bf1c8d3c80fe4acb
Source dataset
uspto-grants-2013_05
Patent number
US08445525B2

Reaction notes

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