Hydrochloric Acid → HCID 131727461, compound

HRID 883582Notes

Reaction equation

HRID 883582 reaction equation
[O:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][C:3]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][N:11]2[CH3:20])=[CH:2]1.[ClH:21].C(OCC)C>C(OCC)(=O)C>[ClH:21].[O:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][C:3]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][N:11]2[CH3:20])=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68995933HCID 68995933, compound

Product 1

HCID 131727461HCID 131727461, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product from Step E (0.12 g, 0.48 mmol) was dissolved in ethyl acetate (2 ml) and treated with 2 M HCl in diethyl ether (0.48 ml, 0.95 mmol) to give 4-Benzofuran-3-yl-2-methyl-1,2,3,4-tetrahydroisoquinoline, hydrochloride salt (0.12 g, 88%, 99.3% AUC HPLC) after filtration: 1H NMR (300 MHz, DMSO-d6) δ 8.18 (br s, 1H), 7.62 (d, J=8.4 Hz, 1H), 6.88-7.36 (m, 7H), 4.90-5.02 (m, 1H), 4.52-4.70 (m, 2H), 3.61-3.82 (m, 2H), 2.95 (s, 3H); EI MS m/z=264 [C18H17NO+H]+. Anal. Calcd. for C18H18ClNO: C, 72.11; H, 6.05; N, 4.67. Found: C, 71.97; H, 6.31; N, 4.52.

Sources & evidence

ORD record
ord-51f1221e4b2e4197a0b855678f9c43fe
Source dataset
uspto-grants-2012_08
Patent number
US08236796B2

Reaction notes

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