Triethylamine → HCID 13279935, compound

HRID 1249180Notes

Reaction equation

HRID 1249180 reaction equation
[CH:1]1([CH2:7][C:8](Cl)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:11][C:12]1[CH:13]=[C:14]([C:19]2([CH:23]([NH2:25])[CH3:24])[CH2:22][CH2:21][CH2:20]2)[CH:15]=[CH:16][C:17]=1[Cl:18].C(N(CC)CC)C>CCOCC>[CH:1]1([CH2:7][CH2:8][NH:25][CH:23]([C:19]2([C:14]3[CH:15]=[CH:16][C:17]([Cl:18])=[C:12]([Cl:11])[CH:13]=3)[CH2:20][CH2:21][CH2:22]2)[CH3:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2757989Cyclohexylacetyl chlorideHCID 130831401-[1-(3,4-Dichlorophenyl)cyclobutyl]ethylamine

Product 1

HCID 13279935HCID 13279935, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Cyclohexylacetyl chloride (3.21 g) in dry ether (100 ml) was added over 30 minutes to a stirred mixture of 1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine (4.88 g), triethylamine (2.5 g) and dry ether (100 ml) at 0°-6° C. After stirring for a further 3 hours the mixture was filtered and the residue was washed with dry ether. The filtrate and washings were combined, dried and evaporated. The residue was dissolved in tetrahydrofuran (50 ml) and the solution heated under reflux in an atmosphere of nitrogen. Borane-methyl sulphide complex (3 ml) was added from a syringe. The resulting mixture was heated under reflux for 12 hours after which it was cooled and ice-water and then 5N hydrochloric acid were added. The organic solvent was removed by evaporation and the residue was cooled, basified with 5N sodium hydroxide solution and extracted with ether. The extracts were washed with water, dried and the ether removed by evaporation. From the residue N-(2-cyclohexylethyl)-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine was obtained by distillation (b.p. 170° C./0.5 mm Hg).

Workup

  1. filtrationwas filtered
  2. washthe residue was washed with dry ether
  3. customdried
  4. customevaporated
  5. dissolutionThe residue was dissolved in tetrahydrofuran (50 ml)
  6. temperaturethe solution heated
  7. temperatureunder reflux in an atmosphere of nitrogen
  8. additionBorane-methyl sulphide complex (3 ml) was added from a syringe
  9. temperatureThe resulting mixture was heated
  10. temperatureunder reflux for 12 hours after which it
  11. temperaturewas cooled
  12. additionice-water and then 5N hydrochloric acid were added
  13. customThe organic solvent was removed by evaporation
  14. temperaturethe residue was cooled
  15. extractionextracted with ether
  16. washThe extracts were washed with water
  17. customdried
  18. customthe ether removed by evaporation

Sources & evidence

ORD record
ord-173c85a14534464f9fd4f5c8c4bec9d9
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

Loading…