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

HRID 1782044
Notes
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Reaction equation

HRID 1782044 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 104424983H-spiro[2-benzofuran-1,4'-piperidine]

Product 1

HCID 187002141'-(Chloroacetyl)-spiro[isobenzofuran-1(3H),4'-piperidine]

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. temperaturecooled in ice
  2. filtrationThe solid was filtered off
  3. washwashed with THF
  4. customThe filtrate was evaporated to dryness
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes