Phthalimide → 2-Phthalimidomethyl-6-(3-dipropylaminopropyl)naphthalene

HRID 348739Notes

Reaction equation

HRID 348739 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][CH2:14][CH2:15][N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH:9]=2)[CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:42]1(=[O:52])[NH:46][C:45](=[O:47])[C:44]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]12.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1>C1COCC1>[C:42]1(=[O:52])[N:46]([CH2:2][C:3]2[CH:12]=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][CH2:14][CH2:15][N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH:9]=3)[CH:4]=2)[C:45](=[O:47])[C:44]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]12

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 230791542-Hydroxymethyl-6-(3-dipropylaminopropyl)naphthaleneHCID 87147022ethyl (NE)-N-ethoxycarbonyliminocarbamate;toluene

Product 1

HCID 230792442-Phthalimidomethyl-6-(3-dipropylaminopropyl)naphthaleneYield 67.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (453 mg) obtained in Example 121-9 was added with triphenylphosphine (516 mg) and phthalimide (245 mg), and then dissolved in anhydrous THF (10 ml). The solution was added with a 40% diethylazodicarboxylate/toluene solution (0.892 ml) in an ice bath and stirred at room temperature for 2 hours under a nitrogen atmosphere. After completion of the reaction, the solvent was distilled off and the residue was then purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (439 mg) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. customthe residue was then purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-578dfb8d54cd4da795aa036e4afe7592
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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