1-Phenethylamine, (+)- → HCID 12050464, compound

HRID 843041Notes

Reaction equation

HRID 843041 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][C@@H:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>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:27][C@@H:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 147378433-Isopropoxy-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dione

Product 1

HCID 12050464HCID 12050464, compoundYield 64.1%

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 (150 g, 0.609 mmol) and (R)-(+)-α-methyl-benzylamine (180 μL, 0.914 mmol) in ethanol (1 mL) were converted to the title compound (120 mg, 64%) m.p.: 158.7-160.1° C.; 1H NMR (DMSO-d6) δ 9.28(d,1H), 8.04(ABq,2H), 7.35(m,5H), 7.10(ABq,2H), 3.83(s,3H), 1.64(d,3H); IR (KBr) 3260, 3060, 3030, 2970, 1770, 1720, 1600, 1560, 1520, 1440, 1410, 1380, 1340, 1310, 1260, 1220, 1180, 1120, 1100, 1025, 825, 700 cm−1; MS (m/z) 307 [M+], [α]25D−185.42° (c0.1049,THF).

Sources & evidence

ORD record
ord-342a8b05c3d74f79b6dd14b7c1bcc3f9
Source dataset
uspto-grants-2002_04
Patent number
US06376555B1

Reaction notes

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