Hydrogen Bromide → HCID 20069068, compound

HRID 982102Notes

Reaction equation

HRID 982102 reaction equation
[ClH:1].[NH2:2][CH2:3][CH:4]1[C:9]2[C:10]([CH3:16])=[CH:11][CH:12]=[C:13]([O:14]C)[C:8]=2[CH2:7][CH:6]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[O:5]1.Br>C(O)(=O)C>[ClH:1].[NH2:2][CH2:3][CH:4]1[C:9]2[C:10]([CH3:16])=[CH:11][CH:12]=[C:13]([OH:14])[C:8]=2[CH2:7][CH:6]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[O:5]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 20069087HCID 20069087, compound

Product 1

HCID 20069068HCID 20069068, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 294 mg (0.9 mmol) of 1-aminomethyl-3-cyclohexyl-3,4-dihydro-5-methoxy-8-methyl-1H-2-benzopyran hydrochloride, from Step 3, in 8 mL of glacial acetic acid and 8 mL of 48% aqueous hydrobromic acid was stirred at reflux temperature for 2 h. The reaction mixture was concentrated in vacuo to remove most of the hydrobromic acid. The aqueous concentrate was adjusted to pH 8.0 with 50% aqueous sodium hydroxide solution and saturated aqueous sodium bicarbonate solution. The resultant aqueous solution was extracted with 2×100 mL of methylene chloride and the combined extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel eluted with 5% methanol in methylene chloride to give the free amine. The amine was treated with diethyl ether saturated with anhydrous hydrogen chloride and the resultant precipitate was crystallized from methanol/ether to afford 152 mg (55% yield) of the title compound, m.p.>280° C.(dec); MS DCI-NH3M/Z: 276 (M+H)+. Analysis calculated for C17H26CINO2 +0.2H2O: C, 64.73; H, 8.42; N, 4.47. Found: C, 64.78; H, 8.33; N, 4.26.

Workup

  1. temperatureat reflux temperature for 2 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto remove most of the hydrobromic acid
  4. concentrationThe aqueous concentrate
  5. extractionThe resultant aqueous solution was extracted with 2×100 mL of methylene chloride
  6. dry with materialthe combined extracts were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified on silica gel
  10. washeluted with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-342023f27c364f8ab35955d7feca8cca
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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