Water → 1'-(5-iodo-1H-benzimidazol-2-yl)spiro[isobenzofuran-1,4'-piperidin]-3-one

HRID 496251

Reaction equation

HRID 496251 reaction equation
Cl[N:2]1[C:6]2[CH:7]=[CH:8][C:9]([I:11])=[CH:10][C:5]=2[N:4]=[CH:3]1.[NH:12]1[CH2:17][CH2:16][C:15]2([C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19](=[O:26])[O:18]2)[CH2:14][CH2:13]1.O>CN1C(=O)CCC1>[I:11][C:9]1[CH:8]=[CH:7][C:6]2[NH:2][C:3]([N:12]3[CH2:17][CH2:16][C:15]4([C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[C:19](=[O:26])[O:18]4)[CH2:14][CH2:13]3)=[N:4][C:5]=2[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 98342553H-spiro(isobenzofuran-1,4'-piperidin)-3-oneHCID 22325322chloro-5-iodo-1H-benzimidazole

Product 1

HCID 1785190321'-(5-iodo-1H-benzimidazol-2-yl)spiro[isobenzofuran-1,4'-piperidin]-3-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Heat a solution of 2 chloro-5-iodo-1H-benzimidazole (3.0 g, 10.7 mmol) and spiro[isobenzofuran-1,4′-piperidin]-3-one (2.63 g, 12.9 mmol) in dry NMP (15 mL) at 100° C. for 14 hours. Pour the cooled mixture into water (50 mL) and extract twice with EtOAc (50 mL). Wash the combined extracts with brine (30 mL), dry, and evaporate in vacuo. Purify by flash column chromatography (50% EtOAc-hexane) to obtain 1′-(5-iodo-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one as a beige solid. C. 1′-(5-Pyridin-3-yl-1G-benzimidazol-2-yl)-spiro[isobenzofuran-1,44′-piperidin]-3-one

Workup

  1. extractionextract twice with EtOAc (50 mL)
  2. washWash the combined extracts with brine (30 mL)
  3. customdry
  4. customevaporate in vacuo
  5. customPurify by flash column chromatography (50% EtOAc-hexane)

Sources & evidence

ORD record
ord-887950b534344fe5a0040ebba87360e7
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Linked notes

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