2-Phenylpropylamine → 3-(4-Methoxy-phenyl)-4-(2-phenyl-propylamino)-cyclobut-3-ene-1,2-dione

HRID 991777Notes

Reaction equation

HRID 991777 reaction equation
C(O[C:5]1[C:6](=[O:18])[C:7](=[O:17])[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(C)C.[CH3:19][CH:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:21][NH2:22]>C(O)C>[CH3:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([C:8]2[C:7](=[O:17])[C:6](=[O:18])[C:5]=2[NH:22][CH2:21][CH:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 113982-PhenylpropylamineHCID 147378433-Isopropoxy-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dione

Product 1

HCID 98185603-(4-Methoxy-phenyl)-4-(2-phenyl-propylamino)-cyclobut-3-ene-1,2-dioneYield 66.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a manner similar to Example 1, Step 2; 3-isopropoxy-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dione (0.150 g, 0.609 mmol) and 2-methyl-2-phenyl-ethylamine (0.165 g, 1.22 mmol) in ethanol (2 mL) were converted to the title compound (0.130 g, 66%) m.p.: 215.4-216.2° C.; 1H NMR (DMSO-d6) δ9.07(br t,1H), 7.95(ABq,2H), 7.30-7.18(m,5H), 7.08(ABq,2H), 3.90-3.72(m,2H), 3.82(s,3H), 3.09,(m,1H), 1.26(d,3H); IR(KBr) 3160, 2960, 1775, 1730, 1560, 1430, 1300, 1250, 1170, 1100, 1020, 840 cm−1; MS (m/z) 322 [M+H+].

Sources & evidence

ORD record
ord-83624b2f17cc45058ad707934279bd49
Source dataset
uspto-grants-2002_10
Patent number
US06465523B1

Reaction notes

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