Hydrochloric Acid → HCID 18477071, compound

HRID 2188207Notes

Reaction equation

HRID 2188207 reaction equation
[C:1]1(=[O:15])[C:14]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][CH2:2]1.[CH2:16]([CH2:23][NH2:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:25]=O.[ClH:27]>C(O)C>[ClH:27].[CH2:16]([CH2:23][NH:24][CH2:25][CH:2]1[CH2:3][CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:12]=[CH:13][C:14]=2[C:1]1=[O:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 1001PhenethylamineHCID 2256831-Oxo-1,2,3,4-tetrahydrophenanthrene

Product 1

HCID 18477071HCID 18477071, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3,4-dihydro-2H-phenanthren-1-one (3.09 g), benzylmethylamine (2.51 g), paraformaldehyde (0.8 g), hydrochloric acid (5 M, 4.76 cm3) and ethyl alcohol (60 cm3) was heated to reflux for 48 h. It was then allowed to cool to room temperature and the alcohol was removed under reduced pressure. Water (100 cm3) was added and the remaining phenanthren-1-one was extracted into diethyl ether (2×100 cm3). The aqueous layer was further extracted with dichloromethane (2×100 cm3) and the combined dichloromethane extracts were dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as a pink solid (3.5 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 h
  3. customthe alcohol was removed under reduced pressure
  4. additionWater (100 cm3) was added
  5. extractionthe remaining phenanthren-1-one was extracted into diethyl ether (2×100 cm3)
  6. extractionThe aqueous layer was further extracted with dichloromethane (2×100 cm3)
  7. dry with materialthe combined dichloromethane extracts were dried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-25720467232a49dda458efa331551a9d
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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