Butanal → 2,3-Dihydro-1,3-dimethyl-2-propyl perimidine

HRID 2372015

Reaction equation

HRID 2372015 reaction equation
[CH3:1][NH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][CH3:14])[CH:6]=[CH:5][CH:4]=1.[CH:15](=O)[CH2:16][CH2:17]C.[C:20]1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>O.O1CCCC1>[CH3:14][N:13]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[N:2]([CH3:20])[CH:1]1[CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 261ButanalHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 140748N,N'-Dimethyl-1,8-naphthalenediamine

Product 1

HCID 199057282,3-Dihydro-1,3-dimethyl-2-propyl perimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N,N'-dimethyl-1,8-naphthalene diamine (prepared in Example 1) (0.93 g, 5 mmol), distilled butyraldehyde (0.43 g, 6 mmol), p-toluene sulfonic acid (5 mg), and tetrahydrofuran (5 ml), was stirred at room temperature for 15 minutes. The mixture was basified with 25% sodium hydroxide (1.0 ml), diluted with water (20 ml) and extracted with ethyl ether (100 ml). The extract was dried over potassium carbonate and concentrated to an oil which was recrystallized from ether-hexane to give crystals of 2,3-dihydro-1,3-dimethyl-2-propyl perimidine: mp 70°-71° C.; NMR (CDCl3) 7.08(m, 4H), 6.29(m, 2H), 4.22(t, 1H), 3.03(s, 6H), 1.4(m, 4H), 0.8(t, 3H); IR (KBr) 1592, 1582 cm-1.

Workup

  1. extractionextracted with ethyl ether (100 ml)
  2. dry with materialThe extract was dried over potassium carbonate
  3. concentrationconcentrated to an oil which
  4. customwas recrystallized from ether-hexane

Sources & evidence

ORD record
ord-0ac0b20b73da4f768285e83a2a21e0a9
Source dataset
uspto-grants-1992_03
Patent number
US05097029

Linked notes

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