N-Iodosuccinimide → 6-cyclopropoxy-8-iodo-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene

HRID 397320Notes

Reaction equation

HRID 397320 reaction equation
[I:1]N1C(=O)CCC1=O.[CH:9]1([O:12][C:13]2[CH:21]=[CH:20][C:19]3[N:18]4[CH2:22][CH2:23][CH2:24][C:17]4=[CH:16][C:15]=3[CH:14]=2)[CH2:11][CH2:10]1>C(#N)C>[CH:9]1([O:12][C:13]2[CH:21]=[CH:20][C:19]3[N:18]4[CH2:22][CH2:23][CH2:24][C:17]4=[C:16]([I:1])[C:15]=3[CH:14]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 230001076-Cyclopropoxy-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene

Product 1

HCID 230001116-cyclopropoxy-8-iodo-2,3-dihydro-1H-3a-aza-cyclopenta[a]indeneYield 72.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

18.5 g N-iodosuccinimide at 0° C. was added to a solution of 17.55 g 6-cyclopropoxy-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene in acetonitrile and the mixture was stirred at this temperature for 15 min. The solid was collected by filtration, washed with cold acetonitrile and dried to constant weight to yield 20.1 g 6-cyclopropoxy-8-iodo-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene as beige crystals melting at 104-105° C.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with cold acetonitrile
  3. customdried to constant weight

Sources & evidence

ORD record
ord-0c9f49d70225419a963bb6fba251828d
Source dataset
uspto-grants-2003_08
Patent number
US06610685B2

Reaction notes

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