Chloroacetyl chloride → 1'-(Chloroacetyl)-spiro[isobenzofuran-1(3H),4'-piperidine]

HRID 1782044Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][C:4]2([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][O:7]2)[CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.[Cl:24][CH2:25][C:26](Cl)=[O:27]>C1COCC1>[Cl:24][CH2:25][C:26]([N:1]1[CH2:6][CH2:5][C:4]2([C:10]3[C:9](=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:8][O:7]2)[CH2:3][CH2:2]1)=[O:27]

Participants

Conditions

Temperature: 20 °C

Procedure

3H-spiro[2-benzofuran-1,4′-piperidine] (5 g, 26 mmol) was dissolved in THF (100 mL) and cooled in ice. Then N-ethyldiisopropylamine (4.94 mL, 29 mmol) and chloroacetyl chloride (2.31 mL, 29 mmol) were added. The mixture was stirred at 20° C. for 15 min. The solid was filtered off and washed with THF. The filtrate was evaporated to dryness and the residue was purified by flash chromatography on silica gel with heptane/AcOEt 70:30. One obtained light yellow crystals (6.5 g, 92%). MS: m/z=266 [M+H]+.

Workup

temperaturecooled in ice
filtrationThe solid was filtered off
washwashed with THF
customThe filtrate was evaporated to dryness
customthe residue was purified by flash chromatography on silica gel with heptane/AcOEt 70:30

Sources & evidence

ORD record: ord-cd6b3608e24a4c67b34d1bea3eb3db73
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07498339B2

Reaction notes

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