Hydrochloric Acid → Racemic 4-benzofuran-2-yl-2,7-dimethyl-1,2,3,4-tetrahydroisoquinoline

HRID 402092

Reaktionsgleichung

Reaktionsgleichung von HRID 402092
[C:1]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)(=O)[CH3:2].[C:13]1([CH3:21])[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][NH2:20])[CH:14]=1.[ClH:22].[CH2:23](OCC)C>>[O:5]1[C:6]2=[CH:12][CH:11]=[CH:10][C:9]2=[CH:7][CH:8]=[C:4]1[CH:1]1[C:2]2[C:16](=[CH:17][CH:18]=[C:13]([CH3:21])[CH:14]=2)[CH2:15][CH2:19][N:20]1[CH3:23].[ClH:22].[O:5]1[C:6]2=[CH:12][CH:11]=[CH:10][C:9]2=[CH:7][CH:8]=[C:4]1[CH:1]1[C:2]2[C:16](=[CH:17][CH:18]=[C:13]([CH3:21])[CH:14]=2)[CH2:15][CH2:19][N:20]1[CH3:23]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 154352-AcetylbenzofuranHCID 660153-Methylbenzylamine

Produkt 2

HCID 68995970Racemic 4-benzofuran-2-yl-2,7-dimethyl-1,2,3,4-tetrahydroisoquinolineHCID 131727460(+)-4-Benzofuran-2-yl-2,7-dimethyl-1,2,3,4-tetrahydroisoquinoline, hydrochloride salt

Versuchsvorschrift

Racemic 4-benzofuran-2-yl-2,7-dimethyl-1,2,3,4-tetrahydroisoquinoline was prepared from 2-acetylbenzofuran and 3-tolylmethylamine as described in Example 26. This racemic compound (105 mg) was separated on semi-prep chiral HPLC (chiralcel OD-H, 1×25 cm, eluent: 3% ethanol in heptane, flow: 4 ml/minute, 500 μl injections, 5 mg/injections). The resulting free bases were dissolved in ethyl acetate and treated with a 2 M solution of HCl in diethyl ether (2 equiv) to give (+)-4-benzofuran-2-yl-2,7-dimethyl-1,2,3,4-tetrahydroisoquinoline, hydrochloride salt (39 mg, 100% AUC HPLC, 99.4% AUC chiral HPLC): 1H NMR (300 MHz, Acetone-d6) δ7.63-7.70 (m, 1H), 7.20-7.47 (m, 6H), 7.00-7.08 (m, 2H), 5.31-5.43 (m, 1H), 4.43-4.62 (m, 2H), 3.70-3.88 (m, 2H), 3.01 (s, 3H); EI MS m/z=277 [C19H19NO]+, [α]25D+20° (c 1.0, MeOH, free base) and (−)-4-benzofuran-2-yl-2,7-dimethyl-1,2,3,4-tetrahydroisoquinoline, hydrochloride salt (40 mg, 100% AUC HPLC, 100% chiral HPLC): 1H NMR (300 MHz, Acetone-d6) δ7.63-7.69 (m, 1H), 7.21-7.47 (m, 6H), 7.00-7.10 (m, 2H), 5.32-5.45 (m, 1H), 4.43-4.66 (m, 2H), 3.67-3.90 (m, 2H), 3.02 (s, 3H); EI MS m/z=277 [C19H19NO]+; [α]25D−17° (c 1.0, MeOH, free base).

Aufarbeitung

  1. customThis racemic compound (105 mg) was separated on semi-prep chiral HPLC (chiralcel OD-H, 1×25 cm, eluent: 3% ethanol in heptane, flow: 4 ml/minute, 500 μl injections, 5 mg/injections)
  2. dissolutionThe resulting free bases were dissolved in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-594df2fefdb9450ea0524210666163a0
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741901B2

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