Hydrochloric Acid → HCID 68601945, compound

HRID 1407811Notes

Reaction equation

HRID 1407811 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]3([CH2:23][O:22][C:21]4[CH:24]=[C:25]5[C:29](=[CH:30][C:20]3=4)[CH2:28][CH2:27][O:26]5)[C:12]2=[O:31])[CH2:6][CH2:5]1)[CH3:3].[ClH:32].O1CCOCC1>CO>[ClH:32].[CH3:3][CH:2]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]3([CH2:23][O:22][C:21]4[CH:24]=[C:25]5[C:29](=[CH:30][C:20]3=4)[CH2:28][CH2:27][O:26]5)[C:12]2=[O:31])[CH2:6][CH2:5]1)[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59352169HCID 59352169, compound

Product 1

HCID 68601945HCID 68601945, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1′-{[1-(1-methylethyl)piperidin-4-yl]methyl}-5,6-dihydrospiro[benzo-[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (0.21 g, 0.49 mmol) and 4 M hydrochloric acid in 1,4-dioxane (0.50 mL, 2.0 mmol) in methanol (1.5 mL) was stirred at ambient temperature for 30 min. The solvent was removed under reduced pressure, the residue was suspended in ethyl acetate/hexanes and the resulting precipitate was collected by filtration. The precipitate was dried to afford 1′-{[1-(1-methylethyl)piperidin-4-yl]methyl}-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one hydrochloride (0.17 g, 76%) as a colorless powder: mp 167° C. (dec.) (hexanes); 1H NMR (300 MHz, CD3OD) δ 7.36 (ddd, J=7.8, 7.2, 1.2 Hz, 1H), 7.19-7.08 (m, 3H), 6.48 (s, 1H), 6.33 (s, 1H), 4.83 (d, J=9.3 Hz, 1H), 4.67 (d, J=9.3 Hz, 1H), 4.51 (t, J=8.6 Hz, 2H), 3.80 (dd, J=14.3, 7.5 Hz, 1H), 3.73 (dd, J=14.3, 7.1 Hz, 1H), 3.54-3.42 (m, 3H), 3.07-2.96 (m, 4H), 2.31-2.16 (m, 1H), 2.09-1.98 (m, 2H), 1.76-1.60 (m, 2H), 1.35 (d, J=6.6 Hz, 6H); 13C NMR (75 MHz, CD3OD) δ180.4, 163.3, 162.9, 143.8, 134.0, 130.1, 124.9, 124.8, 121.5 (2C), 120.1, 110.4, 93.7, 81.8, 73.5, 59.7, 59.3, 49.5, 45.8, 34.1, 29.9, 28.7, 28.67, 17.0; MS (ES+) m/z 419.3 (M+1); Anal. Calcd. for C26H30N2O3.HCl.2H2O: C, 63.60; H, 7.18; N, 5.71. Found: C, 63.80; H, 6.83; N, 5.67.

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationthe resulting precipitate was collected by filtration
  3. customThe precipitate was dried

Sources & evidence

ORD record
ord-3f7d9fe13c284ce68a490378e01fd0f8
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

Loading…