Benzylamine → HCID 58646734, compound

HRID 901987Notes

Reaction equation

HRID 901987 reaction equation
C([O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH:8]1[O:15][CH:9]1[CH2:10]2)(=O)C.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([NH:23][C@@H:8]1[CH2:7][C:6]2[C:11](=[CH:12][CH:13]=[CH:14][C:5]=2[OH:4])[CH2:10][C@H:9]1[OH:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 14948201HCID 14948201, compound

Product 1

HCID 58646734HCID 58646734, compound

Procedure

A mixture of 5-acetoxy-2,3-epoxy-1,2,3,4-tetrahydronaphthalene (prepared in the manner disclosed in U.S. Pat. No. 4,076,843, 20.4 g) and benzylamine (85 mL) was heated in a bomb at 120° C. for 18 h. After cooling, excess amine was distilled off under high vacuum using a 70° C. bath. The semi-solid residue was triturated with chloroform (70 mL) and filtered. The filtercake was washed with chloroform, then with diethyl ether, and dried under vacuum to provide crude product. The crude product was recrystallized from a mixture of methanol and ethyl acetate to yield the title product (10 g) as a white solid. The regioisomeric product (trans 3-benzylamino-2,8-dihydroxy-1,2,3,4-tetrahydronaphthalene) was largely contained in the chloroform extract and wash.

Workup

  1. customprepared in the manner
  2. temperatureAfter cooling
  3. distillationexcess amine was distilled off under high vacuum
  4. customusing a 70° C.
  5. customThe semi-solid residue was triturated with chloroform (70 mL)
  6. filtrationfiltered
  7. washThe filtercake was washed with chloroform
  8. dry with materialwith diethyl ether, and dried under vacuum
  9. customto provide crude product
  10. customThe crude product was recrystallized from a mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-23df66444e5b46b890eb2f6cd57dc135
Source dataset
uspto-grants-2008_04
Patent number
US07365061B2

Reaction notes

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