Benzylamine → HCID 6457799, compound

HRID 1407988Notes

Reaction equation

HRID 1407988 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CC#N>[ClH:1].[CH2:10]([NH:17][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 767274-(2-Chloroethyl)morpholine

Product 1

HCID 6457799HCID 6457799, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 100 mg of N-(2-chloroethyl)morpholine and 575 mg of benzylamine in 5 mL of CH3CN was refluxed for 2 h. The mixture was cooled to 25° C. and partitioned between dichloromethane and an aqueous sodium bicarbonate solution. The organic extracts were dried and the solvent was evaporated. The residual solvent was removed at high vacuum and the residue was dissolved in a large excess of methanolic HCl. The solvent was evaporated to give 60 mg of the product.

Workup

  1. custompartitioned between dichloromethane
  2. customThe organic extracts were dried
  3. customthe solvent was evaporated
  4. customThe residual solvent was removed at high vacuum
  5. dissolutionthe residue was dissolved in a large excess of methanolic HCl
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e2cf8c9b109944db8b404cc283f3644d
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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