Hydrochloric Acid → HCID 21481342, compound

HRID 435769Notes

Reaction equation

HRID 435769 reaction equation
[CH3:1][NH2:2].[O:3]1[CH2:23][CH:4]1[CH2:5][O:6][C:7]1[C:20]2[CH:19]3[CH2:21][CH2:22][CH:12]([C:13]4[C:18]3=[CH:17][CH:16]=[CH:15][CH:14]=4)[C:11]=2[CH:10]=[CH:9][CH:8]=1.[ClH:24]>C(O)(C)C>[ClH:24].[OH:3][CH:4]([CH2:23][NH:2][CH3:1])[CH2:5][O:6][C:7]1[C:20]2[CH:19]3[CH2:21][CH2:22][CH:12]([C:13]4[C:18]3=[CH:17][CH:16]=[CH:15][CH:14]=4)[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 19788336HCID 19788336, compound

Product 1

HCID 21481342HCID 21481342, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 20 g of methylamine in 150 ml of 95% strength alcohol is added all at once to a solution of 12.4 g of 1-[2,3epoxy-propoxy]-9,10-dihydro-9,10-ethano-anthracene. The reaction mixture is subsequently heated to the boil for 12 hours and is then evaporated to dryness. The evaporation residue is recrystallised three times from methylcyclohexane. The base thus obtained, which melts at 128°-129° C, is dissolved in 100 ml of isopropanol by warming, and 35 ml of 2.2 N alcoholic hydrochloric acid are added to the solution. The hydrochloride which precipitates is filtered off, washed with isopropanol and dried at 70°-80° C and 12 mm Hg. 1-[2-Hydroxy-3-methylamino-propoxy]-9,10-dihydro-9,10-ethano-anthracene hydrochloride, thus obtained, melts at 213° C.

Workup

  1. temperatureThe reaction mixture is subsequently heated to the boil for 12 hours
  2. customis then evaporated to dryness
  3. customThe evaporation residue is recrystallised three times from methylcyclohexane
  4. customThe base thus obtained
  5. temperatureby warming
  6. customThe hydrochloride which precipitates
  7. filtrationis filtered off
  8. washwashed with isopropanol
  9. customdried at 70°-80° C

Sources & evidence

ORD record
ord-93d137b05c854fa5ae1941d93755a774
Source dataset
uspto-grants-1977_02
Patent number
US04006184

Reaction notes

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