Hydrochloric Acid → HCID 19775247, compound

HRID 345016Notes

Reaction equation

HRID 345016 reaction equation
Cl[CH2:2][CH:3]1[CH:12]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[CH:5]([C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4]1.[OH:19][CH2:20][CH2:21][NH:22][CH3:23].Cl>C1(C)C(C)=CC=CC=1.CCOCC.C(O)(C)C>[OH:19][CH2:20][CH2:21][N:22]([CH2:2][C:3]1[C:4]2[CH:5]3[CH2:6][CH2:7][CH:8]([C:13]4[C:18]3=[CH:17][CH:16]=[CH:15][CH:14]=4)[C:9]=2[CH:10]=[CH:11][CH:12]=1)[CH3:23]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 80162-(Methylamino)ethanolHCID 285302HCID 285302, compound

Product 1

HCID 19775247HCID 19775247, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 7237O-XyleneSolvent

Procedure

11-Chloromethyl-9,10-dihydro-9,10-ethanoanthracene (45 gm) was combined with 2-hydroxyethylmethylamine (45 gm) in xylene (300 ml) and the mixture heated to reflux for 17 days. The mixture was cooled to room temperature and extracted with 1 N hydrochloric acid (3×100 ml). The combined acid solutions were washed with ether (100 ml), made basic with the addition of 50% sodium hydroxide solution and the mixture extracted with ether (3×100 ml). The combined ether solutions were dried over magnesium sulfate and the ether removed on a rotary evaporator. The residue was distilled (220° C. at 7 mm Hg) to yield a colorless oil. The material was dissolved in ether (200 ml) and treated with 6 N hydrochloric acid in isopropyl alcohol (2 ml). The resulting precipitate was filtered and washed with ether to provide the product. Analytical data are reported in Table I.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 17 days
  3. extractionextracted with 1 N hydrochloric acid (3×100 ml)
  4. washThe combined acid solutions were washed with ether (100 ml)
  5. additionmade basic with the addition of 50% sodium hydroxide solution
  6. extractionthe mixture extracted with ether (3×100 ml)
  7. dry with materialThe combined ether solutions were dried over magnesium sulfate
  8. customthe ether removed on a rotary evaporator
  9. distillationThe residue was distilled (220° C. at 7 mm Hg)
  10. customto yield a colorless oil
  11. filtrationThe resulting precipitate was filtered
  12. washwashed with ether
  13. customto provide the product

Sources & evidence

ORD record
ord-e5df93a402964740bcd163bd458ef100
Source dataset
uspto-grants-1991_10
Patent number
US05055468

Reaction notes

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