Hydrochloric Acid → HCID 18477116, compound

HRID 2188200Notes

Reaction equation

HRID 2188200 reaction equation
[CH2:1]([CH2:8][NH2:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:10].[F:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[CH2:17][CH2:16][CH2:15]2.[CH2:23]=O>C(O)C>[ClH:10].[CH2:1]([CH2:8][NH:9][CH2:23][CH:17]1[CH2:16][CH2:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([F:11])[CH:13]=2)[C:18]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 1001PhenethylamineHCID 149151166-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 18477116HCID 18477116, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice-cooled solution of N-benzylmethylamine (5.67 cm3) in ethyl alcohol (60 cm3) was added hydrochloric acid (5 M, 10 cm3). 6-Fluoro-3,4-dihydro-2H-naphthalene-1-one (6.00 g) and paraformaldehyde (1.32 g) were then added and the resulting mixture was stirred and heated to reflux for 4 h. Upon cooling, the alcohol was removed under reduced pressure and water (100 cm3) was added. The remaining tetralone was extracted into diethyl ether (100 cm3) and the aqueous mixture was then extracted further with dichloromethane (2×100 cm3). The combined extracts were dried (Na2SO4) and concentrated under reduced pressure. Trituration with diethyl ether and filtration provided the title compound (3.18 g) as a white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. temperatureUpon cooling
  4. customthe alcohol was removed under reduced pressure and water (100 cm3)
  5. additionwas added
  6. extractionThe remaining tetralone was extracted into diethyl ether (100 cm3)
  7. extractionthe aqueous mixture was then extracted further with dichloromethane (2×100 cm3)
  8. dry with materialThe combined extracts were dried (Na2SO4)
  9. concentrationconcentrated under reduced pressure
  10. filtrationTrituration with diethyl ether and filtration

Sources & evidence

ORD record
ord-bbb8987766284a5284f65f81e84bdf78
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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