Phthalic Anhydride → HCID 21219216, compound

HRID 1585645Notes

Reaction equation

HRID 1585645 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12]12([CH2:22][NH2:23])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2>C1COCC1>[C:12]12([CH2:22][NH:23][C:4]([C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[C:1]([OH:6])=[O:11])=[O:5])[CH2:19][CH:18]3[CH2:17][CH:16]([CH2:15][CH:14]([CH2:20]3)[CH2:13]1)[CH2:21]2

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamine

Product 1

HCID 21219216HCID 21219216, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Phthalic anhydride (2.65 g, 17.9 mmol) was dissolved in dry THF (50 ml) and a solution of 1-adamantanemethylamine (2.96 g, 17.9 mmol) in THF (50 ml) was added. The mixture was stirred at room temperature for 16 h and the solution evaporated to dryness. The residue was triturated with hexane and the precipitate formed was filtered, washed with hexane and dried to leave the title compound (5.42 g, 97%), 1H NMR (d6 -DMSO) δ 12.9 (1H, s), 8.2 (1H, t), 7.8-7.4 (4H, m), 2.9 (2H, d), 1.9 (3H, s), 1.6 (6H, q), 1.5 (6H, s).

Workup

  1. customthe solution evaporated to dryness
  2. customThe residue was triturated with hexane
  3. customthe precipitate formed
  4. filtrationwas filtered
  5. washwashed with hexane
  6. customdried

Sources & evidence

ORD record
ord-53a5b03721a443b3a9b612ca3fe7d9f6
Source dataset
uspto-grants-1999_08
Patent number
US05939437

Reaction notes

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