Triacetoxyperiodinane → 1-(4-(4-Methylphenyl)-piperazine-1-carbonyl)-cyclopentanecarbaldehyde

HRID 417997Notes

Reaction equation

HRID 417997 reaction equation
[OH:1][CH2:2][C:3]1([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOCC.[OH-].[Na+]>[CH3:22][C:19]1[CH:18]=[CH:17][C:16]([N:13]2[CH2:12][CH2:11][N:10]([C:8]([C:3]3([CH:2]=[O:1])[CH2:4][CH2:5][CH2:6][CH2:7]3)=[O:9])[CH2:15][CH2:14]2)=[CH:21][CH:20]=1

Participants

6

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66651026(1-Hydroxymethyl-cyclopentyl)-(4-(4-methylphenyl)piperazin-1-yl)-methanone

Product 1

HCID 866357821-(4-(4-Methylphenyl)-piperazine-1-carbonyl)-cyclopentanecarbaldehydeYield 105%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

(1-Hydroxymethyl-cyclopentyl)-(4-(4-methylphenyl)piperazin-1-yl)-methanone from the previous step (1.57 g, 5.22 mmol) was dissolved in DCM (40 mL). Dess-Martin periodinane (3.06 g, 7.22 mmol) was added and the reaction mixture was stirred at room temperature for 3.5 hours. The reaction mixture diluted with Et2O (100 mL) and 1M aq NaOH solution (50 mL) was added. The reaction mixture was stirred for 20 minutes and then the organic layer was separated and washed with 1M aq NaOH solution (50 mL), water (50 mL), dried (MgSO4) and concentrated in vacuo to give 1-(4-(4-methylphenyl)-piperazine-1-carbonyl)-cyclopentanecarbaldehyde (1.64 g, 105%) as a brown oil which was used without further purification.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 20 minutes
  3. customthe organic layer was separated
  4. washwashed with 1M aq NaOH solution (50 mL), water (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d0b34e02926f407f95cd2010c108d29b
Source dataset
uspto-grants-2012_01
Patent number
US08093248B2

Reaction notes

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