Potassium Carbonate → HCID 59300165, compound

HRID 2236497Notes

Reaction equation

HRID 2236497 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([OH:9])([CH3:8])[CH3:7].C([O-])([O-])=O.[K+].[K+].[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1)([O-:18])=[O:17]>CC#N>[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:1]2[CH2:5][CH2:4][CH2:3][CH:2]2[C:6]([OH:9])([CH3:8])[CH3:7])=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 12732176a,a-diMethyl-2-PyrrolidineMethanol

Product 1

HCID 59300165HCID 59300165, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Pyrrolidin-2-yl-propan-2-ol (100 mg, 0.78 mmol) is dissolved in CH3CN (5 mL) to which K2CO3 (300 mg, 2.17 mmol) and p-nitrobenzylbromide (250 mg, 1.16 mmol) were added. The resulting mixture is stirred until MS suggested no starting alcohol is present. The suspension is filtered to remove the potassium salts and the acetonitrile is removed under vacuum. The residue is purified to afford the product (105 mg, 51%). 1H NMR (300 MHz, CDCl3) 8.18 (2H, d, J=8.7 Hz), 7.54 (2H, d, J=8.7 Hz), 4.25 (1H, d, J=15 Hz), 3.72 (1H, d, J=15 Hz), 2.90-2.95 (1H, m), 2.76-2.80 (1H, m), 2.28-2.38 (2H, m), 1.71-1.91 (4H, m), 1.24 (3H, s), 1.20 (3H, s).

Workup

  1. additionwere added
  2. filtrationThe suspension is filtered
  3. customto remove the potassium salts
  4. customthe acetonitrile is removed under vacuum
  5. customThe residue is purified

Sources & evidence

ORD record
ord-bacea73eb1b6492f9975f7e80dd1cfe0
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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