HCID 20225018, compound → HCID 20225043, compound

HRID 1249171Notes

Reaction equation

HRID 1249171 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6](=O)[CH2:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1>O1CCCC1>[ClH:18].[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:9][CH2:10][CH2:11]1

Participants

3

Reactant 1

HCID 20225018HCID 20225018, compound

Product 1

HCID 20225043HCID 20225043, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulphide complex (3.4 ml) was added dropwise to a solution of the acetamide (1.6 g) prepared as described above in dry tetrahydrofuran (30 ml). The mixture was heated under reflux for seven hours and then half the solvent removed by evaporation. A mixture of concentrated hydrochloric acid (5 ml) and water (5 ml) was added dropwise with ice-cooling. Water was added and the aqueous layer washed with ether, cooled in ice, basified with 16N sodium hydroxide solution and extracted with ether. The ether extract was washed, dried and the ether removed by evaporation. Hydrogen chloride gas was passed into a solution of a sample of the residue in ether to give N-(2-methoxyethyl)-2-[1-(4-chlorophenyl)cyclobutyl]ethylamine hydrochloride (m.p. 113°-115° C.).

Workup

  1. customprepared
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for seven hours
  4. customhalf the solvent removed by evaporation
  5. additionA mixture of concentrated hydrochloric acid (5 ml) and water (5 ml)
  6. additionwas added dropwise with ice-
  7. temperaturecooling
  8. additionWater was added
  9. washthe aqueous layer washed with ether
  10. temperaturecooled in ice
  11. extractionextracted with ether
  12. extractionThe ether extract
  13. washwas washed
  14. customdried
  15. customthe ether removed by evaporation

Sources & evidence

ORD record
ord-17dd5f56af1b4c94aa0a67e1e2b094fb
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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