Maleic Acid → HCID 131727462, compound

HRID 1983879Notes

Reaction equation

HRID 1983879 reaction equation
[S:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][CH:3]=[C:2]1[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:20])[CH:18]=2)[CH2:13][CH2:12][N:11]1[CH3:21].[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]\[C:25]([OH:27])=[O:26]>C(O)C>[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]\[C:25]([OH:27])=[O:26].[S:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][CH:3]=[C:2]1[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:20])[CH:18]=2)[CH2:13][CH2:12][N:11]1[CH3:21]

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 68996582HCID 68996582, compound

Product 1

HCID 131727462HCID 131727462, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Benzothiophen-2-yl-2,7-dimethyl-1,2,3,4-tetrahydroisoquinoline (0.57 g) was crystallized with maleic acid (1 equiv) in ethanol to give 4-benzothiophen-2-yl-2,7-dimethyl-1,2,3,4-tetrahydroisoquinoline, maleate salt (0.20 g, 26%, 99.5% AUC HPLC): 1H NMR (300 MHz, MeOD) δ 7.76-7.84 (m, 2H), 7.31-7.40 (m, 3H), 7.12-7.18 (m, 3H), 6.25 (s, 2.7H, maleic acid), 5.00 (dd, J=9.6, 6.0 Hz, 1H), 4.58 (d, J=15.3 Hz, 1H), 4.52 (d, J=15.9 Hz, 1H), 3.98 (dd, J=12.3, 5.7 Hz, 1H), 3.74 (dd, J=12.0, 10.2 Hz, 1H), 3.13 (s, 3H), 2.37 (s, 3H), EI MS m/z=294 [C19H19NS+H]+. Anal. Calcd. for C23H23NO4S: C, 64.70; H, 5.43; N, 3.08; S, 7.05 with 0.39% H2O and 1.35 equiv of maleic acid. Found: C, 62.86; H, 5.25; N, 2.90; S, 7.20.

Sources & evidence

ORD record
ord-3a68f1c50f034277bfdd3b4ad99994dd
Source dataset
uspto-grants-2009_06
Patent number
US07541357B2

Reaction notes

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