Hydrochloric Acid → HCID 69520612, compound

HRID 1294650Notes

Reaction equation

HRID 1294650 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:21]=[CH:20][C:10]([O:11][CH:12]3[CH:17]4[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]4)[CH2:13]3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[ClH:24].O1CCOCC1>C(OCC)(=O)C>[ClH:24].[F:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:21]=[CH:20][C:10]([O:11][CH:12]3[CH:17]4[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]4)[CH2:13]3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 11347518HCID 11347518, compound

Product 1

HCID 69520612HCID 69520612, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 6A (230 mg, 0.73 mmol) in ethyl acetate (5 mL) was treated with 4M HCl in 1,4-dioxane (0.5 mL, 2 mmol) to provide the title compound as a solid (106 mg, yield, 42%). 1H NMR (MeOH-d4, 300 MHz) δ 1.79–2.21 (m, 3H), 30 2.32–2.40 (m, 1H), 2.56 (m, 1H), 3.30–3.48 (m, 5H), 3.80 (m, 1H), 4.90 (m, 6.62(dt, J=10.5, 2.4 Hz, 1H), 6.73(dd, J=8.1, 2.3Hz, 1H), 6.78 (tdd, J=8.5, 2.3, 1.0 Hz, 1H), 7.03 (s, 4H), 7.30 (td, J=8.2, 6.7Hz, 1H) ppm. MS (DCl/NH3) m/z 314 (M+H)+. Anal. calculated for C19H20FNO2.1.0HCl: C, 65.23; H, 6.05; N, 4.00. Found: C, 64.96; H, 6.17; N, 3.96.

Sources & evidence

ORD record
ord-bd045a1f90024484a395c321c15ba913
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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