Acetic Acid → 4-Cyclopentylamino-3-methyl-iodobenzene

HRID 891966Notes

Reaction equation

HRID 891966 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.[C:10]1(=O)[CH2:14][CH2:13][CH2:12][CH2:11]1.C(O)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Na].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>O1CCCC1>[CH:10]1([NH:6][C:5]2[CH:7]=[CH:8][C:2]([I:1])=[CH:3][C:4]=2[CH3:9])[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 8452CyclopentanoneHCID 832214-Iodo-o-toluidineHCID 131725371CID 131725371

Product 1

HCID 222410484-Cyclopentylamino-3-methyl-iodobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.5 g (10.7 mmol) of 4-iodo-2-methylaniline, 1.0 ml (11.8 mmol) of cyclo-pentanone, 0.9 ml (16.1 mmol) of glacial acetic acid and 0.1 g of p-toluenesulphonic acid are stirred in 50 ml tetrahydrofuran for 30 minutes. Then 3.1 g (13.9 mmol) of sodium-triacetoxyborohydride are added and the mixture is stirred for a further 26 hours at ambient temperature. The solvent is distilled off and the residue is chromatographed on silica gel, eluting with petroleum ether/ethyl acetate 0 to 10%.

Workup

  1. distillationThe solvent is distilled off
  2. customthe residue is chromatographed on silica gel
  3. washeluting with petroleum ether/ethyl acetate 0 to 10%

Sources & evidence

ORD record
ord-d9cd84dc24ad48ff97ba6e5eacbfbd0e
Source dataset
uspto-grants-2006_02
Patent number
US07005437B2

Reaction notes

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