Thionyl Chloride → 8-Benzyl-1-phenyl-1,8-diaza-spiro[4.5]dec-3-en-2-one

HRID 507868Notes

Reaction equation

[CH2:1]([N:8]1[CH2:25][CH2:24][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14](=[O:22])[CH2:13][CH:12]2O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O>N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:25][CH2:24][C:11]2([N:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:14](=[O:22])[CH:13]=[CH:12]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To 8-benzyl-4-hydroxy-1-phenyl-1,8-diazaspiro[4.5]decan-2-one (400 mg, 1.19 mmol) in pyridine (10 mL) was added thionyl chloride (0.26 g, 3.57 mmol) at 0° C. under N2. The mixture was heated to 50° C. for 5 hours. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc (50 mL) and washed with sat aqueous NaHCO3. The organic layer was separated, dried over Na2SO4 and evaporated to give crude 8-benzyl-1-phenyl-1,8-diaza-spiro[4.5]dec-3-en-2-one, which was purified by column (Petroleum ether/EtOAc 4:1) to give 8-benzyl-1-phenyl-1,8-diaza-spiro[4.5]dec-3-en-2-one. 1H NMR (300 MHz, MeOD) δ 7.89 (d, J=6.0 Hz, 1H), 7.44-7.52 (m, 3H), 7.17-7.27 (m, 5H), 7.14-7.17 (m, 2H), 6.26 (d, J=6.3 Hz, 1H) 3.54 (s, 2H), 2.87-2.91 (m, 2H), 2.35-2.44 (m, 2H), 1.99-2.09 (m, 2H), 1.59-1.64 (m, 2H).

Workup

customThe solvent was removed under reduced pressure
dissolutionThe residue was dissolved in EtOAc (50 mL)
washwashed
customThe organic layer was separated
dry with materialdried over Na2SO4
customevaporated
customto give crude 8-benzyl-1-phenyl-1,8-diaza-spiro[4.5]dec-3-en-2-one, which
customwas purified by column (Petroleum ether/EtOAc 4:1)

Sources & evidence

ORD record: ord-11d2f728a1994a0693e4f4d88d666ba4
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786308B2

Reaction notes

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